20. Smokey and the Bandit (1977)

Burt Reynolds
Sally Field
Jackie Gleason
Jerry Reed

Smokey and the Bandit ain’t nothin BUT a long road trip. With funny turns by Burt Reynolds and Jackie Gleason, it’s no wonder Smokey and the Bandit landed eighth on our list of best action-comedies. Just try and get “Eastbound and Down” outta your head. Sumbitch.

19. The Wizard of Oz (1939)

Judy Garland
Ray Bolger
Jack Haley
Bert Lahr
Billie Burke

Pesky little tornado touches down and turns one girl’s life on its head. Girl and dog meet characters in need of something (a metaphor for how we all need something, right?) as they ease on down the yellow brick road in search of the big man himself, The Wizard. Wicked witch, munchkins and damn flying monkeys pop up like so many obstacles on the road of life. Cue the big musical number and let’s get on with it already.

18. The Straight Story (1999)

Richard Farnsworth
Sissy Spacek
Harry Dean Stanton

This is one unconventional road trip – no buddies along in the backseat – hell, there is no back seat! Richard Farnsworth’s Alvin Straight is on a journey to see his estranged ailing brother and nothing is going to get in his way. It may not be the fastest way to get to point B, but his trusty John Deere makes the six-week trek, Straight meets interesting folks along the way and ultimately he makes it to his brother. Kookiest thing? It’s a David Lynch movie.

17. The Muppet Movie (1979)

The Muppets

Damn if those Muppets aren’t on the ever-lovin’ road trip of a puppet’s lifetime. With a dream to make it big in Hollywood, Kermit the Frog embarks on a journey that introduces him to the rest of the Muppety gang, and they travel in and out of precarious situations (Doc Hopper, anyone?). But ultimately, it’s all good. The pig gets her frog and the big musical number finale says it all.

16. The Darjeeling Limited (2007)

Owen Wilson
Adrien Brody
Jason Schwartzman

Three brothers embark on a journey aboard the Darjeeling Limited train – a spiritual trip across India that brings the estranged siblings together. In quirky Wes Anderson form, a runaway snake and pepper spray fit into the quirky comedy well, getting the trio booted from the train and stranded in the desert with all their baggage. Owen Wilson, Adrien Brody, and Jason Schwartzman play the brothers to perfection, as their trip back to civilization puts them in touch with their lost connection.

15. Rain Man (1988)

Dustin Hoffman
Tom Cruise
Valeria Golino

Assy Charlie Babbitt (Tom Cruise) discovers that the autistic brother he never knew, Raymond (Dustin Hoffman), inherited his father’s fortune, so he kidnaps Ray and they set off on a road trip (Ray won’t fly) like no other. from Kmart underwear, to the People’s Court, those friggin spilled toothpicks (hey, it’s Bonnie Hunt as the waitress!) and a side trip to count cards in Vegas, Charlie learns more about his special brother and a load about himself, realizing the estate money really isn’t that important after all.

14. Tommy Boy (1995)

Chris Farley
David Spade
Rob Lowe
Julie Warner
Dan Aykroyd

Chris Farley and David Spade hit the open road as two lame-ass salesmen hoping to save Farley’s dad’s auto parts company from “auto parts king” Ray Zalinsky (Dan Aykroyd). The unlikely buddy teaming is prickly at first, but somehow Farley’s loveable dufus finds his way into Spade’s uptight heart and they make beautiful music together on the road, sell brake pads… and of course, save the company!

13. Pee-Wee’s Big Adventure (1985)

Paul Reubens
Elizabeth Daily
Mark Holton
Diane Salinger

Somebody stole Pee-Wee Herman’s bicycle and there’ll be hell to pay when he takes to the road in search of the thief and his stunning prized possession. An early directorial feature from Tim Burton, Pee-Wee’s Big Adventure takes the viewer along for the ride, as Herman has run-ins with a ghost trucker, bikers and a jealous boyfriend too. Just remember “Be sure and tell ‘em Large Marge sent ya!”

12. Apocalypse Now (1979)

Martin Sheen
Marlon Brando
Robert Duvall

Again, this “road trip” entry is about the journey, as Captain Willard (Martin Sheen) travels the Cambodian jungle and the Nung River to “terminate with extreme prejudice” the renegade Colonel Kurtz (Brando), who is waging his own personal war against the Vietnamese with native troops. Willard’s journey is physical and spiritual, and director Francis Ford Coppola pulls out the best performances in his ensemble cast.

11. Easy Rider (1969)

Peter Fonda
Dennis Hopper
Jack Nicholson

This is it. THE road trip movie of the 60s. Get your motor runnin’… as bikers Wyatt and Billy set off on a road trip across America to Mardi Gras, in search of America and freedom. A total trip, with some highs and lows… bigotry, hitchhikers, jail, a lawyer and death among them… but Easy Rider is never anything less than pure road trip goodness.

10. Dumb and Dumber (1994)

Jim Carrey
Jeff Daniels
Lauren Holly

Two morons take it on the road from Rhode Island to Aspen, Colorado (”where the beer flows like wine”)… and we never do really find out which one is dumb and which one dumber in this Farrelly brothers gross-out comedy classic. Jim Carrey and Jeff Daniels shine in this asshole buddy comedy, with classics like “wanna hear the most annoying sound in the world” and… well, a little revenge that lands Jeff Daniels’ Harry on the toilet in one of the most explosive bathroom scenes ever.

9. Harold and Kumar go to White Castle (2004)

John Cho
Kal Penn
Neil Patrick Harris

Stoners on the road get sidetracked by all sorts of adventures on their way to the elusive White Castle. Things are anything but dull in this ultimate quest to cure the munchies – with extra fun from Neil Patrick Harris. Who doesn’t love Harold and Kumar? (It’s number four on Movie Crunch’s 20 Best Stoner Movies of All Time, so we have much love!)

8. Sideways (2004)

Paul Giamatti
Thomas Haden Church
Virginia Madsen
Sandra Oh

A road trip in wine country? Middle aged schlubs can take road trips too! Yep, two loser-ish dudes travel the wine trail and discover a bunch about themselves, their friendship and relationships with women. Can this road trip provide the enlightenment to accept their failures and move on to better things? Paul Giamatti is brilliant as ever… plus Sideways made Pinot Noir the total “it” wine, so that’s something.

7. Into the Wild (2007)

Emile Hirsch
Marcia Gay Harden
William Hurt
Jena Malone
Catherine Keener

What happens when someone who seemingly has it all going for him gives it all up for a journey of self-exploration? Into the Wild is the amazing true story of Christopher McCandless, a recent college grad who abandons his possessions and savings account to travel to Alaska on a quest for life’s truth. Along the way, McCandless meets a number of people that enrich his life and ultimately he learns being a loner isn’t such a great thing… in the end, scribbling in his book: “Happiness only real when shared.”

6. Little Miss Sunshine (2006)

Greg Kinnear
Steve Carell
Toni Collette
Paul Dano
Abigail Breslin
Alan Arkin

A dysfunctional family on (dysfunctional) wheels, Little Miss Sunshine is one of those true quirky indie film gems, with a great cast in Steve Carell, Abigail Breslin, Greg Kinnear,Toni Collette, Paul Dano, and of course, Alan Arkin as Grandpa. There’s nothing like being in close proximity to your crazy relatives in a barely functioning VW van (there’s gotta be a metaphor in there somewhere).

5. Thelma and Louise (1991)

Susan Sarandon
Geena Davis
Harvey Keitel
Brad Pitt

Shame on you if you think a chick flick can’t make the list of great road trip movies. A two-day vacation quickly goes all kinds of wrong – forcing these besties to go on the run from the long arm of the law. Thelma and Louise are two broads hitting the road for a tale that puts never-ending friendship to the test. And ultimately, over the edge. Friends ‘til the goddamn end, that’s for sure.

4. The Motorcycle Diaries (2004)

Gael García Bernal
Rodrigo de la Serna

The Motorcycle Diaries is nothing but road trip, reliving the journals of Cuban Revolution leader Che Guevara and his best friend as they traveled South America by motorcycle in the early 1950s. There’s an amazing story here that exposes the men to the divide between societal classes, plus the rich cinematography brings the story truly alive. OK, enough of the film geekiness… moving on…

3. Planes, Trains & Automobiles (1987)

Steve Martin
John Candy

Getting home for Thanksgiving has never been such a pain in the ass, but Neal Page (Steve Martin) quickly realizes that his bad luck demands him to have to play nicely and share rides with the most annoying of road trip buddies, Del Griffith (John Candy). Steve Martin and John Candy are the perfect comedic pairing – here’s just one of the movie’s great scenes:

2. Vacation (1983)

Chevy Chase
Beverly D’Angelo
Anthony Michael Hall
Dana Barron

If this isn’t the perfect road trip flick, we don’t know what is. The Griswold family is on a cross-country pilgrimage to see Marty Moose at Walley World – planning to hit as many of the U.S. wonders along the way in their trusty family truckster as is humanly possible. A side visit with Cousin Eddie adds Aunt Edna and pooch to the list of passengers… and after she and the dog bite it, they finally get to their destination. But, oh frak… it’s closed. Ultimately, you can bet that nothing is getting in the way of Clark Griswold’s family having a good time.

1. The Lord of the Rings Trilogy (2001/2002/2003)

Elijah Wood
Ian McKellen
Viggo Mortensen
Sean Astin
Orlando Bloom
Hugo Weaving
Andy Serkis
Sean Bean

Shit, what a long, long road to Mordor and Mount Doom. It’s like the mother of all road trips, spanning three movies to get the One Ring to point B. While The Lord of the Rings trilogy isn’t a conventional road trip, the journey is certainly long and there’s plenty of adventure and obstacles along the way. Any way you slice it, LOTR is one hell of an ultimate road trip.

Clearly, Kal Penn isn’t taking a page from the Joaquin Phoenix playbook, who recently quit acting to pursue a crappy rap career.

So, what’s the story with Kal Penn’s White House job?

Penn, 31, told the press today, “I won’t be acting while I’m working at the White House.” He’s currently looking for a place to live in Washington and says his start date is “up in the air.”

Kal Penn’s new job will be as associate director in the Office of Public Liaison, where he’ll “go to communities and “continue the dialogue starting during the campaign.”

20. Saving Grace

Cast:
Brenda Blethyn
Craig Ferguson

Somewhere among the stoner humor comes an intelligent film about weed. Watching refined British ladies get totally stoned during a tea party is reason enough to check this one out. Recent widow Grace (Brenda Blethyn) has to raise money to pay the huge debt left by her dead husband and save her home. Aided by her Scottish gardener (Craig Ferguson), she turns his small marijuana crop into booming business.

19. Rolling Kansas

Cast:
James Roday
Sam Huntington
Jay Paulson
Charlie Finn

Directed and co-written by actor Thomas Haden Church (of TV’s Wings and the movie Sideways), Rolling Kansas looks at three brothers’ (and their friends) quest for a magical marijuana forest that can solve all of their financial woes. While there’s not much actual pot smoking in the film, the search for a goldmine of government marijuana puts Rolling Kansas firmly in our top 20 list. Plus there’s all the makings of a crazy road trip with the promise of a pot-filled happy ending.

18. Homegrown

Cast:
Billy Bob Thornton
John Lithgow
Hank Azaria

OK, so you’re not going to find your lighthearted buddy stoner comedy in Homegrown, but that doesn’t mean you should pass it by. A little bit comedy, drama and thriller combined, Homegrown follows a trio of bumbling pot farmers as they try and conduct business as usual when their boss is murdered. Millions of dollars are at stake, but nothing is simple, naturally, as Jack (Billy Bob Thornton), Carter (Hank Azaria) and Harlan (Ryan Phillipe) take matters into their own inept hands and just get deeper in shit.

17. Super High Me

Cast:
Doug Benson

Super High Me takes Morgan Spurlock’s concept of eating McDonald’s for 30 days straight and replaces burgers and fries with pot. Comedian Doug Benson tackles this documentary head-on, first avoiding pot for 30 days before taking on the challenge of smoking it for 30 days. What does he discover in the process? He continues to work his stand up gigs and goes through a battery of tests to see how getting stoned daily impacts his life – he experiences weight gain and decreased lung capacity, but his intelligence scores and sperm count go up (go figure). Not a lot of scientific evidence here, but a good time anyway.

16. Reefer Madness

Cast:
Dorothy Short
Lillian Miles
Dave O’Brien
Thelma White

This 1935 propaganda flick was supposed to scare the crap outta wannabe potheads, but Reefer Madness instead became a cult classic. Watch what happens when you smoke marijuana – the horror! The crazed behavior! Beware the perils of pot. Hmm… doesn’t quite seem like it made the impression they hoped, but it’s good for a laugh now, if only to see the wild results of getting high. How many people did Reefer Madness deter from the ills of pot? We’re guessing not many.

15. Dude ,Where’s My Car?

Cast:
Ashton Kutcher
Seann William Scott
Jennifer Garner
Marla Sokoloff

Proof positive that getting baked makes you lose shit, Ashton Kutcher epitomized the stoner dude to perfection in “Dude, Where’s My Car?” Sure, Kutcher and Sean William Scott are complete dipshits, but isn’t that part of the fun? Say you’re above this mediocre pothead flick and we’ll call you a liar. Just try not to laugh at how stupid Jesse and Chester are and the ridiculous plot (Seriously… aliens?) – stupid, yeah. But funny too. We’re especially entertained by the Chinese drive-through restaurant lady “And then?…” Bonus points for pre-famous Jennifer Garner.

14. PCU

Cast:
Jeremy Piven
David Spade
Chris Young
Jon Favreau

While it’s not strictly a pothead movie, PCU has elements of stoner activity among the n’er-do-wells of The Pit and the campus potheads, who spend their days playing Frisbee. Add in a pre-swingers Jon Favreau who epitomizes the stoner sent on a fool’s errand to get the beer (but ends up picking his nose in a parking lot). Among the great dialog is the miscommunication from an old lady on the street as heard by stoned Gutter – he interprets her “Can you show me where the campus is” as “Can you blow me where the pampers is?” Ultimately, Gutter saves the day when George Clinton and Parliament-Funkadelic stumble upon the Favreau character and agree to play at their party and save the failing slacker house from being shut down.

13.Knocked Up

Cast:
Seth Rogen
Katherine Heigl
Paul Rudd
Leslie Mann

While not the central plot line of Knocked Up, the sub-plot involving a group of stoners trying to get a web site a la Mr. Skin up and running provides some of the funniest scenes in the film. Seth Rogen delivers the stoner persona of Ben Stone well – conflicted by having to put his pothead ways behind him and become more responsible as he prepares for a baby. Breaking away from his stoner pals (Jay Baruchel, Jonah Hill, Jason Segel and Martin Starr) is hard to do because they’re just too much frickin fun. Check out the gag reel:

12. How High

Cast:
Method Man
Redman
Mike Epps

Silas P. Silas (Method Man) and Jamal King (Redman) smoke their friend. Well… sort of. When pal Ivory dies, Silas uses his ashes as fertilizer for growing marijuana. The pair smoke the pot – and in doing so, the ghost of Ivory is summoned, conveniently giving them the answers to their college entrance exam. They get by with a little help from a (dead) friend, landing acceptance to Harvard… but naturally, the magical weed is stolen and their luck runs out.

11. Fast Times at Ridgemont High

Cast:
Sean Penn
Jennifer Jason Leigh
Judge Reinhold
Phoebe Cates
Ray Walston

Is there no stoner cooler than Jeff Spicoli, played to hilarious effect by Sean Penn? From the first moment we spy the pothead surfer, to his well-known movie quote: “All I need is some tasty waves, a cool buzz and I’m fine” – Fast Times gave us a taste of just how laid back a stoner can be. Bonus cool points for Spicoli’s exchanges with history teacher Mr. Hand, who is convinced all his students are smoking dope. Spicoli to Mr. Hand: “Hey bud, what’s your problem?”

10. Half Baked

Cast:
Dave Chappelle
Guillermo Díaz
Jim Breuer
Harland Williams

If there’s anything that Jim Breuer is good at (and trust us, there’s not much water in his talent pool), it’s playing the half-baked halfwit. The comedic genius of Dave Chapelle gives the otherwise mediocre film a boost, plus appearances by Steven Wright, Tommy Chong, Janeane Garofalo, Willie Nelson, Tracy Morgan, Snoop Dogg, Jon Stewart, Stephen Baldwin and Bob Saget don’t hurt either. Thurgood (Chappelle) and his friends Brian (Breuer) and Scarface (Diaz) need to bail their friend Kenny (Harland Williams) out of jail but don’t have the cash, naturally. The slackers steal medical marijuana from the lab where Thurgood works and start their own business, called Mr. Nice Guy. A local drug dealer threatensto kill the guys for stealing business. Oh, and a pouch of Jerry Garcia’s ashes figures nicely into the plot too.

9. Jay and Silent Bob Strike Back

Cast:
Jason Mewes
Kevin Smith
Shannon Elizabeth

If there’s one thing Kevin Smith carried through his many films, it’s the continuity of lazy stoners Jay and Silent Bob. The pair of slackers are featured in their own adventure in Jay and Silent Bob Strike Back, with the guys on a mission to get the money rightfully owed to them for the making of a “Bluntman and Chronic” movie – or shut it down completely. This is the farthest from standing in front of convenience stores the pair have traveled… and in Jay and Silent Bob Strike Back, it’s the potheads who save the day!

8. Tenacious D in The Pick of Destiny

Cast:
Jack Black
Kyle Gass
Dave Grohl

Kick ass music, Jack Black, Kyle Gass , weed and psychedelic mushrooms. What more could you ask for in Tenacious D’s search for the coveted Pick of Destiny – a chip from the tooth of Satan himself? Their quest for the magical pick leads them to the ultimate showdown against Satan, played by Dave Grohl. But will they possess the magical power of the pick, rock open mic and win the prize to pay their rent? Hey, at least they nab Satan’s horn and create the “Bong of Destiny.”

7. Pineapple Express

Cast:
Seth Rogen
James Franco
Gary Cole
Rosie Perez
Danny McBride

Just released this week, Judd Apatow’s Pineapple Express is part stoner buddy comedy, part action flick, — but guaranteed to deliver laughs as it follows dealer and pothead in an unlikely adventure. Starring Seth Rogen as pot consumer Dale to James Franco’s pot dealer Saul, the two potheads end up on the run from a bad cop (Rosie Perez) and drug lord (Gary Cole) after Saul is witness to a murder. Seth Rogan naturally draws on his stoner experience and James Franco shows a funnier side over some of his serious roles. Pineapple Express is a new rare strain of weed that Saul explains is so special “it’s almost a shame to smoke it…it’s like killing a unicorn.”

6. Grandma’s Boy

Cast:
Allen Covert
Nick Swardson
Doris Roberts
Linda Cardellini

Lest you think that Grandma’s Boy is the story of a mild-mannered guy who still idolizes his gramma, think again. Starring Allen Covert, who typically appears in pal Adam Sandler’s flicks, this Grandma’s Boy shows he can carry a stoner flick just by being the loveable loser. Passed over by critics and movie audiences, Grandma’s Boy stars Covert as Alex, a 35-year-old video game tester who loves to smoke pot with his roommate Josh. Only Josh spends all the rent money on hookers and the pair get tossed out of their place. Alex goes to live with grandma and her two friends (Doris Roberts, Shirley Jones and Shirley Knight). And, well, it’s totally dumb and immature. But so funny.

5. Friday

Cast:
Ice Cube
Chris Tucker
Nia Long
Bernie Mac
John Witherspoon

There’s more to Friday than two guys getting high and sitting on their front porch on a Friday. Friday became an instant stoner hit with the hilarious roles played by Ice Cube and Chris Tucker. Ice Cube’s Craig Jones is fired on his day off, while Chris Tucker’s Smokey is in a bit of trouble. Stoners often face an obstacle in these films – in this case, the guys have to figure out how to get $200 to repay drug dealer Big Worm by 10 p.m. on Friday (because Smokey smoked the pot he was supposed to sell) – or be killed. Two sequels, Next Friday and Friday After Next, followed.

4. Harold and Kumar Go to White Castle/Harold and Kumar Escape from Guantanamo Bay

Cast:
Kal Penn
John Cho

A big shout out has to be given to both Harold and Kumar films – the original is the ultimate stoner munchy run gone awry. After getting stoned, pals Harold and Kumar go in search of the White Castle burger, which seems like a simple enough task. Hilarity ensues, including Neil Patrick Harris in all his Doogie Howser ecstasy glory and the boys score a giant bag of weed (the discovery sets off a montage of Kumar hanging out with the bag, having sex, getting married and working through marital problems with his new love). The second installment of Harold and Kumar finds the boys mistaken as terrorists when their bong looks like a bomb to passengers aboard a flight to Amsterdam.

3. Up in Smoke

Cast:
Cheech Marin
Tommy Chong

Cheech and Chong prove they are the godfathers of weed by taking their comedy routine to the big screen in their first full-length movie. With so many Cheech and Chong stoner flicks to choose from, we went with the original and probably the best of the series, Up in Smoke, if only for the prestigious honor of having the biggest joint in film history. For your viewing enjoyment, check out the video clip below, where Cheech declares “I can smoke anything” of his special blend made with Labrador (part marijuana, part dog feces ’cause his dog ate his stash):

2. The Big Lebowski

Cast:
Jeff Bridges
John Goodman
Steve Buscemi
Julianne Moore

The Big Lebowski delivers more than stoner one-liners, giving thoughtful consideration to what it is that makes “The Dude” (played with laid-back precision by Jeff Bridges) tick. While plenty have criticized this Coen Brothers classic for being one of the weakest of their films, plenty of fans (hey, there’s even a Lebowski Fest!) sit back and enjoy the ride after a case of mistaken identity for The Dude sets him on an adventure he didn’t sign on for. After all, he’s just The Dude.

1. Dazed and Confused

Cast:
Jason London
Rory Cochrane
Adam Goldberg
Matthew McConaughey
Milla Jovovich
Ben Affleck
Parker Posey

It doesn’t get much better than this – following 70’s era high school kids on their last day of school. Dazed and Confused is more than getting high on the last day of school – there’s a lot of coming of age shit going on too that rounds this out to a great little movie. Among the circle of life (outgoing seniors hazing incoming freshman) and the look at all of your stereotypical highschool types (nerds, jocks, stoners, cheerleaders), you’ve got funny stuff like Ron Slater’s (Rory Cochrane) take on George and Martha Washington getting high: “Every day George would come home, she’d have a big fat bowl waiting for him, man. She was a hip hip hip lady.” Also notable is the pre-all-star cast here, including Ben Affleck, Adam Goldberg, Matthew Mcconaughey, Milla Jovovich, Joey Lauren Adams, and Parker Posey.