| Video Title | Time | HD | Description | Added | |
|---|---|---|---|---|---|
| 1 | 'Sideways' Theatrical Trailer | 2:30 | Oct 4, 2004 | ||
| 2 | "Here's To A Great Week" | 0:50 | Before Jack's (Thomas Haden Church) wedding, Miles (Paul Giamatti) takes him on a vacation. (Thomas Haden Church) |
Oct 4, 2004 | |
| 3 | "Are You Chewing Gum?" | 1:27 | Miles (Paul Giamatti) teaches Jack (Thomas Haden Church) how to taste wine properly. |
Oct 4, 2004 | |
| 4 | "Windmill" | 1:45 | Miles (Paul Giamatti) and Jack (Thomas Haden Church) catch up with Maya (Virginia Madsen), an old friend. |
Oct 4, 2004 | |
| 5 | "I Need To Be Spanked" | 1:36 | Miles (Paul Giamatti) and Jack (Thomas Haden Church) taste wine with Stephanie (Sandra Oh). |
Oct 4, 2004 | |
| 6 | "What's Your Novel About?" | 1:22 | Covering up a lie, Miles (Paul Giamatti) tries to explain his novel to Maya (Virginia Madsen). |
Oct 4, 2004 | |
| 7 | "This Is Going To Be Fun" | 1:50 | Jack (Thomas Haden Church) and Miles (Paul Giamatti) become hostile on the golf course. |
Oct 4, 2004 | |
| 8 | "I'm Not Drinking Merlot" | 0:57 | Jack (Thomas Haden Church) attempts to calm down Miles (Paul Giamatti) before a date. |
Oct 4, 2004 | |
| 9 | "The Day After Yesterday" | 2:35 | Thomas Haden Church and Paul Giamatti explains an intimate scene between Giamatti and Virginia Madsen. |
Apr 5, 2005 | |
| 10 | "Sticking Together" | 1:03 | Director Alexander Payne and actors Paul Giamatti and Thomas Haden Church discuss what drew them towards the film. |
Apr 5, 2005 | |
| 11 | "Chemistry" | 1:43 | Actors Virginia Madsen, Paul Giamatti, and Thomas Haden Church and Director Alexander Payne discuss the close relationships formed on the set. |
Apr 5, 2005 |
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