In 1999 Denzel Washington was nominated for an Academy Award for his portrayal of Rubin "Hurricane" Carter. Carter was convicted of murdering two people in a bar and grill in Paterson, New Jersey in 1966. Twenty-two years later Carter was set free and the court dismissed the original court charges. Although many people learned of Carter's story in this bio-pic , others we already familiar with the murders in Dylan's song "Hurricane" off his 1976 album Desire. Dylan was quoted to say that it was his best protest song in over a decade and performed the number every night on his Rolling Thunder Review tour.

It was about three years after Dylan's comeback with his album Time Out of Mind that he composed the song "Things Have Changed" for Curtis Hanson's film Wonder Boys. Not only was his newest compilation featured on the soundtrack but another assortment of Dylan tunes including "Not Dark Yet" off his latest Grammy award winning album. Although the film was not a major commercial success it received critical praise for both the actors and its impressive soundtrack. Dylan went on to win an Academy Award for Best Original Song; after winning the Oscar Dylan has brought the award on tour with him where it stands atop of his amplifier.

Legendary filmmaker Sam Peckinpah who directed The Wild Bunch and The Getaway created this modern western in hopes of creating the greatest film in that genre. But his consumption of alcohol lead to difficulties on the set and caused the film to go over budget and over schedule. The studio ended up cutting over twenty minutes of the film out and the critical and audience reception was not favorable. The film was re-released with the original print intact and has been regarded as an overlooked classic. James Coburn and Kris Kristofferson play the two leads with Dylan in the supporting cast as well as composer of the film's score.

Filmed during Dylan's 1966 tour of the United Kingdom with his backup band The Hawks (later to become The Band), Dylan collaborated with D.A. Pennebaker with whom he worked with previously on the documentary Don't Look Back. After seeing the final cut Dylan thought the film mimicked Don't Look Back and re-edited the film himself and his associate Howard Alk. The film never aired and bootleg copies have been circulating amongst Dylonologists for decades. If you can get a hold of a copy you can see a first hand look at the time of Dylan's life that was represented by Cate Blanchett in Todd Haynes' I'm Not There. Though mostly scatter-brained and sloppily put together, the film has some great live performances and a drug induced rant with John Lennon in the back of limousine.

Dylan co-wrote this film with collaborator and director Larry Charles who later went on to direct the Borat motion picture. Shot in only twenty days in digital video the film features an all star line-up including Jeff Bridges, John Goodman, Penelope Cruz, and Luke Wilson who all took a pay cut to collaborate with Dylan in the movie. Although the film was attacked left and right by critics and a majority of the audience the film is a treat to see Dylan playing the aging rock star just released out of prison. The soundtrack is the films saving grace with a re-recorded version of "Cold Iron's Bound" and covers by Jerry Garcia and the Grateful Dead, Los Lobos, and Italian hip-hop group, Articolo 31, creating their own take on "Like a Rolling Stone."