Counterculture icon and Hollywood legend Dennis Hopper has passed away due to complications from prostate cancer. Hopper was 74 years old.

Dennis Hopper was known throughout much of his nearly six-decade career as a Hollywood rebel. Indeed, Hopper’s 1969 film Easy Rider, which he also directed and co-wrote with Peter Fonda, is viewed by many film scholars as the ultimate anti-establishment film and one of the primary movies responsible for sparking the “New Hollywood” film movement in the 1960s and 1970s.

After the success of Easy Rider, Hopper’s mainstream career faltered somewhat due to drug and alcohol abuse, as well as a desire to direct and perform mainly in independent film. With the exception of Apocalypse Now in 1979, Hopper didn’t have a notable role until the 1980s when he decided to enter himself into drug rehabilitation. During this decade, Hopper again achieved widespread recognition for his turns in David Lynch’s Blue Velvet and the sports classic Hoosiers.

Throughout the 1990s, Hopper utilized his manic energy and forceful acting style to great effect playing a number of villainous roles, including the psychotic bomber in the 1994 blockbuster action film Speed and the head of the “Smokers” in Kevin Costner’s ill-fated 1995 film Waterworld. In the last years of his life, Dennis Hopper found success on television, including a short, but critically acclaimed role on 24.

From the 1950s through the new millennium, few actors have made their mark in Hollywood quite as strongly as Dennis Hopper. In tribute to his life, we have put together a list of our top five favorite Dennis Hopper films. Check out our list below with clips included (be advised there is some NSFW language).

Speed (1994)

In Speed, Dennis Hopper plays an ex-cop and former bomb squad technician who holds a bus full of people ransom with an ingenious plot device – if the bus goes below 50 miles per hour, it will blow up. The film, which also starred Keanu Reeves and Sandra Bullock, was a huge international blockbuster, earning $350 million worldwide.

It also spawned the classic Dennis Hopper line, “Pop quiz hotshot.”

Apocalypse Now (1979)

It’s a miracle that Apocalypse Now was ever actually made (watch the brilliant documentary Hearts of Darkness to see how messed up the production was), but we’re certainly glad it was since it gave us one of Dennis Hopper’s finest performances. Playing a manic combat photographer, Hopper’s drug-crazed rants about Kurtz (Marlon Brando’s character) are enough to make you feel like you’ve dropped some acid yourself.

Blue Velvet (1986)

David Lynch’s surreal mystery film Blue Velvet gave us another drug-addled Dennis Hopper role. As the criminal Frank Booth, Dennis Hopper inhales nitrous oxide and sexually abuses Isabella Rossellini’s character in a variety of disturbing ways. It was a strange part, but one that Hopper knocked out of the park, notching another iconic role in his belt.

Watch the now-famous scene of Hopper becoming emotionally overwhelmed by Roy Orbison’s “In Dreams.”

Hoosiers (1986)

One of my personal favorites, and one of the greatest sports films of all time, Hoosiers gave Dennis Hopper the rare opportunity to portray a sympathetic character. As Shooter, Hopper channeled his own experience with substance abuse to play the reclusive alcoholic father of one of Gene Hackman’s basketball players.

The scene where Hopper listens to the final game from the hospital where he has finally admitted himself for rehab always brings a smile to my face. Hopper earned a Best Supporting Actor Academy Award nomination for his role.

Easy Rider (1969)

As I mentioned at the beginning of the post, Dennis Hopper’s Easy Rider is arguably the most important counterculture film of the 1960s. Easy Rider tells the story of two bikers Wyatt (Peter Fonda) and Billy (Hopper) who ride across the United States to make it to Mardi Gras. During their trip, we get a drug-fueled glimpse of how the “Free Love” generation polarized America. (Easy Rider is also notable for being Jack Nicholson’s first big break as an actor.)

There are countless excellent scenes to choose from, but Easy Rider‘s opening credits, set to the strains of Steppenwolf’s “Born to Be Wild,” are particularly memorable.

Honorable Mention

True Romance (1993)

Tony Scott’s slick crime film True Romance has a truly great ensemble cast, featuring Christian Slater, Patricia Arquette, Brad Pitt, Gary Oldman, Val Kilmer, Christopher Walken, James Gandolfini, and, of course, Dennis Hopper. While he doesn’t play a major role in the movie, Hopper does have one of the best scenes in the movie opposite Christopher Walken. Not only is an example of both actors at the top of their game, but it is also some of Quentin Tarantino’s best writing.

Dennis Hopper was a truly great actor, and he has certainly left his mark on Hollywood. Besides our list, what are some of your other favorite Hopper roles?