The Beginner’s Guide to iTunes

For the inexperienced user, the task of getting media content loaded onto your iPod or iPhone can be a daunting one, and even for the experienced computer user, the way in which Apple has approached media management in the world of the iPod and iTunes may differ significantly from what you’ve become accustomed to.
This tutorial will provide the information that both the novice and experienced computer user may find useful as they take their first trepidatious foray into the world of iTunes and the iPod, including where to get music and video content from, how to get it onto your iPod, and how to manage and organize it once it’s there.
iTunes and Apple’s Philosophy of iPod Media Management
Prior to delving into filling your iPod, it is important to understand that Apple takes a considerably different approach from many other media software and hardware products in terms of how media content is managed, both on your computer, and on the iPod itself.
Content on the iPod is managed via Apple’s iTunes software application, which is a free download from Apple’s web site. However, iTunes is more than just a means of loading your iPod. It is in fact an entire media management system that is designed to organize and catalog your music, audiobooks, videos, podcasts, and more. In fact, iTunes doesn’t even require that the user have an iPod, and there are many people out there who choose to use iTunes simply as their media management application.
Philosophically, the iTunes library is treated as the central point of all media content, and devices such as the iPod, iPhone, and even the Apple TV are considered extensions of this core iTunes library. The idea here is that you manage the content in a master library on your computer, and carry around portions of it on your portable device. This is different from the concept of the portable media player being the core library that many experienced users of other media products have become accustomed to.
In its default configuration, iTunes automatically synchronizes your library (or a portion thereof), to your iPod. Once setup, this happens transparently and automatically each time you connect your iPod to your computer. Again, the iPod becomes an extension of your main library, rather than the library itself.
All of this having been said, iTunes does provide a method for users who would rather not maintain an iTunes library on their local computer, but simply want to manually transfer music from one or more computers to their iPod on an as-required basis. We will discuss these options in more detail further on in this article.
Regardless of the method used, generally the first step in getting content onto your iPod is to get it into your iTunes library. In fact, if you do not yet own an iPod but are planning to buy one, you can even download iTunes in advance and start importing your media content and getting your library ready for your iPod. Then, when you finally do get your iPod, filling it up is generally as simple as connecting it to your computer and letting iTunes do the rest.
It’s all about the Music…
Today’s iPod models can play music, audiobooks, podcasts, videos, and even display your photo collection. However, despite all of these different types of content, the core focus remains on music, and most iPod owners will be concerned first and foremost with getting their existing music collection onto their iPod.
One of the common myths about the iPod is that you have to buy your music from the iTunes Store. This stems at least partly from the fact that iTunes is actually both the name of the iPod management application and the name of Apple’s online media service, and also partly from the fact that some of Apple’s competitors have propagated this myth by implying that it costs a lot of money to fill an iPod.
In reality, nothing could be further from the truth. Both the iPod and iTunes will happily import content from commercial or self-created audio CDs, or any standard MP3 file that you may have available. Purchasing content from the iTunes Store is far from the only option, and there are many iPod users with large music collections who have never purchased even a single track from the iTunes Store. Further, as more online digital music stores begin adopting open DRM-free standards, you have many other choices for where to purchase music, even for online download. Our Guide to Purchasing Music Online provides more detail on the various options available ranging from the iTunes Store to other services like Amazon and Walmart.
However, since most people who buy an iPod probably already own at least some music on compact disc (CD), this is usually a good place to start. iTunes provides built-in capabilities for loading your CDs into directly into your music library. Further, if you have an Internet connection iTunes can even look up track information for most commercial CDs and fill it for you automatically, ensuring that any tracks you import are properly labelled.
iTunes can also natively import any files that are already in the AAC or MP3 format which can be obtained from any number of online sources. Our Guide to Free Music for your iPod discusses a number of options for obtaining free legal digital music downloads, and a Consolidated List of Free Music Websites can also be found in our iLounge Discussion Forums.
In fact, the only real limitation with regards to the iPod’s support for digital music formats is the Windows Media Audio (WMA) format. Neither iTunes nor the iPod natively support this format, although iTunes will helpfully offer to convert any unprotected WMA files that it finds. Unfortunately, if you have purchased files in the Windows Media Audio (WMA) format from other online music services, iTunes will not be able to convert these directly due to the Digital Rights Management (DRM) restrictions on these files. If your DRM license permits, you can burn these to an audio CD using another compatible media application and then import that audio CD into iTunes as you would for any commercial audio CD.
The iTunes Store is certainly a convenient option for purchasing digital music, and this is even more true with Apple’s transition to an entirely DRM-free music catalogue earlier this year. Music available on the iTunes Store is no longer protected by any Digital Rights Management (DRM), and therefore any concern about only being able to use your purchased music on Apple devices is no longer an issue. Tracks purchased from the iTunes Store are tagged with your iTunes Store account information for various reasons such as keeping track of your purchases within the iTunes application, but even this information can be easily removed by a third-party application if it’s a privacy concern. Keep in mind also that the DRM-free catalog only applies to music files; other content types such as audiobooks, movies, and TV shows remain DRM protected.
Importing existing digital music files into iTunes
This section provides information for users who have an existing collection of digital music files that they would like to add to their iTunes library. New users who are starting out with no digital music files can skip ahead to the next section on importing CDs into iTunes.
The first time you run iTunes, it will helpfully offer to scan your entire computer for any compatible audio files and import them into your iTunes library.

You can let iTunes do this for you, or you can skip this step and add these files manually later. If you let iTunes scan your hard drive for MP3/AAC/WMA files, you may end up with a lot more than you anticipated. Many games and other applications will have soundtracks and effects tracks stored in the MP3 format within their program folders, and iTunes may end up adding these to your library along with your normal music files.
Further, you may wish to adjust some of iTunes’ settings prior to this first import. We generally recommend that users skip this initial import process. Don’t worry, it’s just as simple to scan your hard drive and add these files in later, after you know what you may be getting yourself into.
For users with a relatively small number of digital music files, the default options will normally suffice, and there’s probably no need to be concerned with the more detailed information explained below.
However, for those users who already have a large collection of existing digital music files, it is important to first understand how iTunes handles this process, and where you may want to adjust some of these options. While any of the default import options will usually get your music into iTunes with a minimum of initial effort, a little bit of pre-planning can ensure that your music library is more manageable in the long run, and can avoid surprises later on.
Note that iTunes’ default behavior for importing music files is slightly different on Windows than it is on the Mac.
For Mac users, iTunes stores all music files that you add to your iTunes library by default in its own “iTunes Media Folder” location, which is in an “iTunes/iTunes Media” sub-folder structure within your home directory’s “Music” folder. When you add existing digital music files to the iTunes library, these files are copied from their present location into the iTunes Media Folder. This means that if you are importing a large music collection, you will need enough disk space to make a complete copy of it during this process. Once your music has been added to iTunes and copied into the iTunes Media Folder, you can delete the original files, however.
For Windows users, iTunes also creates an itunes Media Folder in “iTunesiTunes Music” under your Windows “My Music” folder, but does not copy existing digital media files into this location. Rather, by default it simply leaves them where they are and references them from there.
The location of the iTunes Music folder, and whether added files are copied or not can be adjusted through iTunes’ advanced preferences, which can be accessed from the iTunes, Preferences menu on Mac OS X, or the Edit, Preferences menu on Windows. Simply select the “Advanced” and “General” tab from the iTunes Preferences dialog box:

The Copy files to iTunes Music folder when adding to library option determines whether iTunes copies added files into the music folder path or simply references them from their original locations. This option is enabled by default for Mac users, and disabled by default for Windows users.
The Keep iTunes Music folder organized option determines whether iTunes will attempt to reorganize files within the iTunes Music folder as the track information is modified within iTunes itself. When this option is enabled, iTunes will read the ARTIST, ALBUM, and TRACK name information from your media files and use this to organize them into a sub-folder structure in the form of ARTISTALBUMTRACKNAME. This naming behavior is hard-coded and cannot be modified. This only affects existing files already in the iTunes Music folder. Files copied in as they are added are always placed in the organized location.
For Mac users, this option will be enabled by default, Windows users are given an opportunity to specify whether they want this option enabled or not as part of the initial iTunes Setup wizard:

Also keep in mind that regardless of the “Keep organized” setting, iTunes will never attempt to move, rename, or delete any files that are located outside of the iTunes Music folder. Essentially, iTunes considers this music folder to be its “home” directory and considers any files that are not stored in this location to be outside of its control.
With the “Copy files” and “Keep organized” settings enabled, iTunes is designed to insulate the average user from the underlying file system, taking care of all of the details of how your media files are stored for you such that you don’t normally have to worry about it. As changes are made to track information within the iTunes library, iTunes automatically reorganizes the underlying music files appropriately.
Once you’ve reviewed these settings and decided how you would like your media files to be organized, you can begin the process of adding existing files to your iTunes library simply by selecting the appropriate option from the File menu in iTunes. This is another area where Windows and Mac versions differ slightly—Mac users simply get a single Add to Library option, whereas Windows users must choose between Add File to Library and Add Folder to Library.

Regardless of which operating system or method you use, however, the concept is the same—simply select a file, files, or a folder to add to your library, and iTunes does the rest. Note that if you are selecting a folder, all sub-folders are also included.
Another method for adding music files to your iTunes library is simply to drag and drop either individual files, a group of files, or a folder right into the iTunes window. These files will be added to the iTunes library in the same way that the File menu options work.
Two last points that should be noted:

• Unlike some other media management applications, iTunes does not have any kind of “Watched Folder” feature that will allow you to have downloaded MP3/AAC files automatically added to your iTunes library. The only way to add tracks into the iTunes library is to do so manually by using the File, Add to Library option or dragging and dropping them into the iTunes window.
• Likewise, iTunes does not track iTunes files that are renamed or moved outside of iTunes. The iTunes library stores information to files based on the full path and filename. Once a file has been imported into the iTunes library, renaming or moving that file will cause iTunes to lose track of it. If you plan to use your own file and folder structure, this should ideally be established before you import these tracks into the iTunes library.

Importing CDs into iTunes
For many new iPod users, this may be their first journey into the world of digital music, and they won’t necessarily have a large pre-existing library of digital music files. However, just about everybody has a few CDs that they want to get into their iTunes library. Fortunately, this process is extremely simple in iTunes.
Importing a CD into your iTunes library is generally as simple as inserting the CD and letting iTunes do the rest. When you insert a CD, iTunes detects it, looks up its track information online and simply asks you if you want to import it:

Simply select “Yes” and iTunes will import the tracks into your iTunes library, storing them as 256kbps AAC files in your iTunes Music folder.

When you insert a CD, iTunes will attempt to look up information on the CD using the Gracenote CD Database (CDDB). If multiple matches are found, it will prompt you to select the correct one:

 

 

  If iTunes cannot find any matches, then it will inform you of this, and ask you if you want to import the songs anyway. In this case, you might want to answer “No” so that you can enter information for the CD manually before proceeding to import it.

 

All of these settings can be further tweaked in your iTunes preferences. On the General tab you can specify how iTunes behaves when you insert an audio CD:

The option, “When you Insert a CD” allows you to specify what iTunes should do when you insert an audio CD. You can choose to do nothing more than simply show the CD contents, start playing the CD, or automatically import the CD. In particular, the “Import CD and Eject” option is a very efficient way to import a large number of CDs. In this mode, iTunes will automatically import any audio CD that you insert, and eject it when it’s finished. With this option you can just keep feeding CDs into your computer and letting iTunes work through them in the background while you’re working on something else.

The Automatically retrieve CD track names from Internet allows you to disable the CDDB lookup for newly-inserted CDs. Note that you can always initiate a manual lookup of CD information from the iTunes Advanced menu. Lastly, the Import Settings button opens a new window that allows you to specify your default audio file format and bit-rate for your imported CDs.

iTunes supports the AAC, AIFF, Apple Lossless, MP3 and WAV file formats. Presets are provided for each format that should meet a typical user’s needs, although you can choose to customize your import settings more precisely if you so desire by selecting the “Custom” option in the Settings drop-down menu.

Although there is much debate and discussion about the merits of various audio formats and bit-rates, a simple rule of thumb is that iTunes’ AAC encoder will produce slightly better quality audio files at a given bit-rate (ie, file size) than iTunes’ MP3 encoder will, but you will sacrifice compatibility with many other digital audio hardware and software players, as MP3 is a much more widely-supported format.
In short, if you only intend to play your imported music through iTunes or on your iPod (or other Apple device), then you can select the AAC format. For a more compatible library with other hardware and software, you will probably want to use the MP3 format.
The other formats (AIFF, Apple Lossless and WAV) will create significantly larger file sizes, as these are essentially “lossless” compression. These formats are generally only of interest to higher-end users and audiophiles.
More information and discussion on the various audio file formats can be found in our Digital Audio Formats forum in the iLounge Discussion Forums.
Buying Digital Music
Another possible source of music for your iPod is commercial music sources such as the iTunes Store itself or other third-party digital music services such as Amazon or Walmart.
The iTunes Store itself works within the iTunes software application, and any music purchased from the iTunes Store is automatically downloaded and added to your iTunes library. More detailed information on purchasing content from the iTunes Store can be found in our Complete Guide to Using the iTunes Store.
Note that some commercial digital music services still use the Protected WMA format for their music, which is not compatible with iTunes or the iPod. There are a few emerging services, however, such as eMusic (http://www.emusic.com) and more recently the Amazon Digital Music Store (http://www.amazon.com) which now offer digital music for sale in a non-DRM-protected standard MP3 format. These files contain no copy protection or other restrictions, and can be played on any player which supports the almost-universal MP3 file format. Our Guide to Purchasing Music Online provides more information on the various online music stores that are compatible with iTunes and the iPod.
Music purchased from other online sources will simply be downloaded to your hard drive, and must be added manually to iTunes in the same way as any other digital music file.
Audiobooks
iTunes and the iPod also provide support for audiobooks purchased from the iTunes Store or from Audible.com. These can be downloaded/imported directly into iTunes, and listened to via iTunes or on your iPod or iPhone. Note that Audible.com audiobooks are not compatible with the Apple TV.
You can also import your own books on CD into the iTunes library in much the same way as you would import any other CD. These will not be organized into the “Audiobooks” section in iTunes by default, however, but will be treated as music files. In recent versions of iTunes, however, you can easily catalogue these imported files as audiobooks.
For more information on audiobook support in iTunes and on the iPod, including instructions for how to convert your own audiobooks into iTunes, see our Complete Guide to iTunes Audiobooks, Podcasts + iTunes U and our Books and Spoken Word forum in the iLounge Discussion Forums.
Podcasts and iTunes U
Another great source of iPod content can be found in the iTunes Podcast directory and the iTunes U Educational Section within the iTunes Store. Podcasts are audio or video tracks, usually of an episodic nature, that you subscribe to. These include such things as news broadcasts, talk radio shows, audio and video blogs and more. iTunes U content is very similar to podcasts, but these are distributed by educational institutions such as colleges and universities and contain educational content and course materials.

Podcasts and iTunes U are accessed via the iTunes Store, however they are generally available at no cost. In fact, Apple really only provides the catalogue for this content; the content itself is downloaded directly from the provider’s own web site.
Once you subscribe to a podcast or iTunes U collection, iTunes will automatically download new episodes as they become available, and transfer these to your iPod if you have configured it to do so.
For more information on podcast support in iTunes and on the iPod, see our Complete Guide to iTunes Audiobooks, Podcasts + iTunes U and our Podcasts & Podcasting forum in the iLounge Discussion Forums.
Organizing it all
Once you have imported your music into your iTunes library, you may still want to organize it to make information easier to find.
iTunes and the iPod index your music by tag information contained within the files such as artist, album, and track name, rather than simply by file and directory name. Music imported from CD or purchased from legitimate online digital music stores should already have this information correctly filled in. However, often users who have collected music files from a variety of different sources may find that the information contained within the files themselves is inaccurate or incomplete. This information can be cleaned up in iTunes itself simply by selecting a file or group of files and choosing Get Info from the iTunes File menu, which will present a dialog box where you can edit the information for that track or group of tracks.

Alternatively, for more comprehensive re-tagging solutions, there are third-party tools available that can help to automatically transfer a file/folder naming structure into the internal tag information within the files themselves. Tag & Rename ($30, 30-day trial available) or MP3Tag (donation-ware).
Current iPod models also offer the ability to add album artwork to your music files which will be displayed on the iPod. iTunes can automatically search for missing album artwork for your tracks assuming that the album and artist information is accurate. This feature requires an iTunes Store account, but is free to use. Alternatively, artwork can be added manually through each track’s file information properties, in the same way that other tags are edited.
In addition to organizing the tag information within files themselves, it may also be desirable to create playlists within the iTunes application to organize your favorite songs, or select groupings of music to transfer to your iPod. To create a playlist, simply choose File, New Playlist from within iTunes. You can then add content to the playlist by dragging and dropping it from your main iTunes library window. The advantage of playlists is that these not only provide an organization for your music within iTunes and the iPod, but they can also be used a method for automatically synchronizing only selected content from your iTunes library onto your iPod. This is especially useful when you have a library that is significantly larger than the capacity of your iPod.
Further, iTunes also offers a more advanced method of playlist—the Smart Playlist. This is a dynamic playlist that you can create which automatically selects tracks based on search criteria you specify, and when combined with iTunes’ ratings and play tracking features can be easily setup to create dynamic playlists to keep your iPod content fresh.
For more information on tagging your music tracks, adding album artwork to them, and creating playlists, see our Complete Guide to Album Tagging, Art and Playlists in iTunes.
Putting it on your iPod
So, once you’ve collected some music in your iTunes library, and you’ve unwrapped your new iPod, the next step is to transfer the music onto your iPod. Again, this is an area where iTunes makes things incredibly simple if you already have an organized iTunes library.
Simply connect your iPod to your computer. By default, iTunes will detect the new iPod, and take you through some initial screens to set up your iPod.

From here you can specify a name for your new iPod, and whether you want iTunes to automatically sync music and/or photo content or not (more on photo content a bit later). Note that you can easily rename your iPod later simply by double-clicking on it in the iTunes Devices list to edit the name and typing in a new name.
If your iPod is large enough to hold your entire iTunes library, this is really the only step. Click “Done” and iTunes will proceed to synchronize your entire music library onto your iPod, including any playlists that you have created.
By default, iTunes simply tries to synchronize everything in your iTunes library onto your iPod. This works well for many users, and is by far the simplest solution. In this mode, your iTunes music library and your iPod are essentially mirrored copies of each other, including all of your playlists from your iTunes library. Any new tracks you add to your iTunes library are added to your iPod, and any tracks you delete are removed from your iPod. Further, information on ratings, last played times, and play counts are transferred from the iPod back to your iTunes library, as is the saved playback position in any audiobooks or podcasts you have listened to.
On the other hand, if your music library is larger than the capacity of your iPod, iTunes will notify you of this and simply automatically select music to place on your iPod to fill the available free space.

iTunes uses your song and album rating information to try and select your preferred content, grouping whole albums as much as possible. While this is a good way to quickly get some initial content onto your iPod, iTunes’ selections are often more random than anything else.
Once this playlist has been created, however, you can adjust the content as you would any other playlist. When you next connect your iPod, any content you have removed from this playlist will be removed from your iPod, and any new content you have added to this playlist will be added to your iPod.
What this automated process actually does, however, is set your iPod up to synchronize only selected playlists—specifically only the single playlist that it has automatically created for you. Although you can continue to manage your iPod content through this single playlist, most users won’t find this to be particularly practical, as this precludes you from adding any additional playlists to the iPod.
Fortunately, you can adjust these synchronization settings yourself, and choose additional playlists to synchronize. This is done by connecting the iPod, and selecting it in the iTunes source pane on the left-hand side. Doing so will present a “Summary” view of your iPod, with a list of tabs across the top of the screen showing the different content types that you can synchronize with your iPod.

Simply select the “Music” tab and you will be shown the options for automatically synchronizing your music content.

From here, you can choose to sync Selected playlists, artists, and genres and simply place a checkmark beside each playlist, artist or genre that you would like to synchronize with the iPod. ONLY the content in those areas and the playlist entries themselves will be transferred to the iPod.
Since this is synchronization, changing this setting will also remove any content that is no longer selected. So if you change your iPod from Entire music library to Selected playlists, artists, and genres then content that is not in any of the areas you select is going to be removed from the iPod during the next synchronization.
Note also the option to Automatically fill free space with songs. As the name implies, this option will automatically fill any remaining space on your iPod with a selection of tracks from your music library. In fact, when iTunes detects that your library is larger than the capacity of your iPod, it selects this option automatically with no further playlists, artists, or genres selected. You can refine this option further by selecting the specific items you want on your iPod, and leave the Automatically fill free space… option enabled to keep any remaining space filled up with additional content.
With automatic synchronization, it is important to understand that you never actually manage the content directly on the iPod itself. If you want to remove a track from the iPod, you simply remove it from your iTunes library or remove it from the playlist that is syncing with your iPod (if you are syncing using selected playlists), and iTunes then removes it from the iPod during the next synchronization. With automatic sync, there should never be content on your iPod itself that is not also located in your iTunes library, and in fact any content removed from your iTunes library will also be removed from the iPod, as it will continue to be a mirror image of either your entire library or those playlists, artists and genres which you have selected for synchronization.
Manual Mode
There are two significant considerations with automatic synchronization that might be a limitation for some iPod users.
Firstly, since automatic synchronization mirrors the content of your iTunes library onto your iPod, it stands to reason that you must actually have an iTunes library on your computer and maintain this library. This may not be practical for users with limited disk space.
Secondly, automatic synchronization only works with one iTunes library. Your iPod in essence becomes “linked” to your iTunes library, making it difficult to manage your iPod and load music onto it from more than one computer. In fact, if you connect an iPod set to automatically synchronize with a given iTunes library to another computer running iTunes, it will notify you that your iPod is already associated with another library, and prompt you to erase your iPod if you want to sync it with the new library:

In either case, switching your iPod into “manual mode” can be a possible solution. In this mode, your iPod essentially becomes its own distinct portable library. There is no longer any association between your iTunes library and your iPod, and you manage content on the iPod itself directly.To set the iPod to manual mode, simply check the box labelled Manually manage music and videos found on the iPod “Summary” page within iTunes, and click the “Apply” button.

Once in manual mode, you add content to the iPod simply by dragging it from the iTunes library directly onto your iPod icon in the iTunes source pane, in much the same way that you would add content to a playlist. Further, you can view and manage the content on the iPod directly by clicking on the small triangle that appears to the left of the iPod icon in the source pane. This will expand the folders on the iPod itself to show the categories of content and playlists stored on the iPod. You can then create new playlists, modify the properties of any given track or even delete it from the iPod completely in the same way as you would in the iTunes library itself.

The manual mode setting travels with the iPod. Once manual mode is enabled, it will remain enabled on any other iTunes library that you connect your iPod to. This will allow you to easily manage your iPod content and add new content from more than one computer.
Keep in mind that in manual mode, information such as rating, play count and last played time will NOT normally be transferred back to your main iTunes library, but will only be stored on the iPod device itself. This may limit the usefulness of Smart Playlists that rely on this information within your main iTunes library.
Note that the one thing you cannot do in manual mode is transfer music from the iPod back to your computer. iTunes itself provides some support for transferring tracks that were purchased from the iTunes Store, but for all other types of content, the transfer is a one-way process. For more information on solutions for copying content from your iPod back to your computer, see our article, Copying Content from your iPod to your Computer.
Further, manual mode only applies to music and video content. In manual mode, podcast and iTunes U content can be transferred to an iPod manually, but the settings on the Podcasts and iTunes U tabs will also remain selected and provide automatic synchronization as well. Other types of content such as Applications, Games, Photos, and Contact/Calendar information is always synchronized automatically, however. Manual mode is also exclusive to the iPod and iPhone—the Apple TV does not support manual management of content.

  Note that the iPhone’s manual mode works differently from the iPod models, including the iPod touch. Although you can manage content on the iPhone manually with current iPhone OS and iTunes versions, you cannot use the iPhone in manual mode on more than one computer at a time. Connecting the iPhone to a second computer will show manual mode as being disabled, and attempting to enable manual mode on a second computer will prompt you to erase your content from the iPhone to pair it with the new computer.

Finally, one important caveat: The iPod and iPhone are portable devices that can easily be subject to loss or damage. If manual mode is being used as a method of maintaining the ONLY copy of your library on your iPod, it is STRONGLY recommended that additional backups be kept either on an external hard drive or DVD. Losing or damaging your iPod is bad enough, but losing your entire music library in the process would be much worse.
About Video Content
Video capabilities were first introduced to the iPod family in 2005 with the release of the fifth-generation iPod. Today all of the current iPod models, with the obvious exception of the Shuffle, now support video playback as well.
Most of the basic concepts for synchronizing video content to the iPod work in much the same way as synchronizing audio content. Content is imported into the iTunes library, managed via iTunes, and then synchronized to the iPod via either the various automatic synchronization options, or manually through drag-and-drop.
Unfortunately, sources of video content are somewhat more limited, as iTunes does not provide any facility to import DVD video into the iTunes library. Therefore, for many users the only legitimate and easy source of video content becomes the iTunes Store, although there are other solutions available for converting video content into an iTunes and iPod ready format.
The following articles provide comprehensive details on converting, importing, and managing video content in iTunes and on the iPod:

  The Complete Guide to iPod, Apple TV and iPhone Video Formats

  The Complete Guide to iPod, iPhone and Apple TV Video Conversion (Mac)

  The Complete Guide to iPod, iPhone and Apple TV Video Conversion (Windows)

  The Complete Guide to Managing iTunes Videos

About Photos
In October 2004, Apple added the ability for a new model of fourth-generation iPod to display photos and photo slideshows, a feature that has now become standard on all iPod models.
Photo synchronization works via iTunes, but is handled very differently from other media types. For more information on synchronizing photos to your iPod, see our Complete Guide to Displaying Photos on iPod + iPhone.
About Games and Applications
The enhanced fifth-generation iPod introduced in Septmeber of 2006 introduced the ability for the iPod to support additional games that could be purchased from the iTunes Store. This is presently the only available source of iPod Games, and like most music and video content purchased from the iTunes Store, the iPod must be “authorized” to play the games with the same account that was used to purchase them. Similarly, an App Store was introduced for the iPhone and iPod touch in July 2008, providing a wealth of third-party applications to enhance the functionality of these devices. The App Store continues to be the only legitimate source of iPhone and iPod touch applications, and these applications are protected by the same DRM used for other iTunes Store content.
iPod Games are always synchronized to the iPod automatically, and can be controlled via the “Games” tab in your iPod’s settings in iTunes. Likewise, Applications for the iPhone and iPod touch are also always synchronized automatically, and can be configured via the “Applications” tab for your iPhone or iPod touch in iTunes. Further, iTunes 9 provides the ability to reorganize which screens your applications are shown on from within this settings screen.