1. "Thelma and Louise" (1991) — Two morals in Ridley Scott's controversial film: rednecks are rednecks, so don't trust one in a parking lot. Second, dump the loser husband before you have to take a dive into the Grand Canyon. Great blowing-up-the-18-wheeler scene. Remastered DVD includes a "chick track" with commentary by stars Geena Davis and Susan Sarandon and screenwriter Callie Khouri and a deleted argument about beef jerky between the two lead characters.
2. "The Straight Story" (1999) — Richard Farnsworth stars in one of the coolest road-trip movies ever, and the convertible is actually a souped-up riding mower. One adventure after another, one amazing character after another, and director David Lynch didn't even need to spill blood to keep you riveted.
3. "Road Trip (2000) — OK, like a dumb-ass, you accidentally mail off an illicit tape to your girlfriend 1,800 miles away. What to do? You and three of your dumbest friends hit the road to retrieve it. A Tom Green insta-classic.
4. "Midnight Run" (1988) — Bobby DeNiro plays a bounty hunter, competing with a rival bounty hunter (John Ashton) out to catch a Mafia accountant (Charles Grodin) on a cross-country chase. And you thought you had a friggin' bad day.
5. "Boys on the Side" (1995) — Whoopi Goldberg, Mary-Louise Parker and Drew Barrymore are three screwed-up women who end up tripping across the country together. Herbert Ross' film is a lot more serious than the trailer let on—involving lesbianism, AIDS and bad lays—and only part of the movie's an actual road trip. But it's a great chick flick, and the soundtrack will get any woman out of a slump.
6. "Easy Rider" (1969) — If you've never seen it, rent it now. Two '60s hippie types—Dennis Hopper and Peter Fonda—take off on motorcycles and cross paths with all sorts of weird characters out in Middle America. The performance by a young Jack Nicholson as the "law'er with the ACLU" is worth the cost of the rental.
7. "True Romance" (1993) — Clarence and Alabama (Christian Slater and Patricia Arquette) are naïve newlyweds running from the mob, coming across an all-star cast of bad guys and freaks. Brad Pitt's stoner guy may be his best role to date. Written by Quentin Tarantino so the bloodletting is witty and hip.
8. "Bonnie & Clyde" (1967) — Road trips don't get more passionate than this! Faye Dunaway and Warren Beatty rob and run, run and rob. The ending ain't pretty, but the two of them sure are.
9. "A Perfect World" (1993) — Easily Kevin Costner's best movie (because, in part, he didn't direct it; Clint Eastwood did), this film is superbly written, directed and acted. In the film, an ex-con kidnaps a little boy and holds him hostage across Texas, and the little boy helps him find his humanity. One of the more powerful crime scenes in film comes near the end, as the boy looks on.
10. "Lost in America" (1985) — A New York couple decides to chuck their success and "do" America in a Winnebago. Laugh hysterically as the city slickers fail miserably. Great scene with a pimply-faced, teenage fast-food manager.
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