Road Trip movies are some of the most unexpected gems over the past decades, as they usually sneak up on you–but they are definitely at the top of my list as some of the greatest comedies of all time.  Here’s my list for the top 15:

15 – Oh Brother Where Art Thou (2000)

A Coen Brother’s classic, you probably wouldn’t think about this being a road movie…but it is.  It’s also based on, arguably the biggest literary road trip…Homer’s The Odyssey!  Although Homer is given a co-writing credit on the film, Joel Coen and Ethan Coen claim never to have read “The Odyssey” and are familiar with it only through cultural osmosis and film adaptations. The title of this movie didn’t come from the book at all, but rather another movie. “O Brother Where Art Thou?” comes from the title of the movie-within-a-movie in Preston Sturges’ Sullivan’s Travels (1941). John Turturro has called this movie “a hillbilly musical comedy adventure.”

14 – Sideways (2004)

You would probably be surprised to find out that Paul Giamatti and Thomas Haden Church had to audition for their roles in the film. You’d be even more surprised to find out that for the scene that Thomas Haden Church read for during the audition, it called for the actor to strip naked, which he did and was later surprised to find out that out of all the actors who auditioned for the same part with the same scene…he was the ONLY one to strip naked. And it got him the role. George Clooney campaigned for the part of Jack, but Alexander Payne thought Clooney was too big a star. However, Clooney got to play the lead in Payne’s next full feature, The Descendants (2011). Paul Giamatti admitted to faking every bit of wine knowledge, and not understanding why anybody would care about it. He also claims he was shocked that he was cast in a lead role and initially thought it was a practical joke. Paul Giamatti admitted in interviews that he doesn’t like wine.

13 – Kingpin (1996)

The Farrelly brothers bowled a strike with this one. It came out the same year as the Big Lebowski and I have to admit liking this one just a touch better. As is the case with most of his films, Bill Murray ad-libbed virtually every line he spoke. He would read over the script, get the “general” idea, and then discard it. The Farrelly brothers, on the DVD commentary, said that they’re very glad he did because it was funnier. Turned out, Bill was also a very good bowler. Bill Murray really bowled three strikes in a row in the scene where his character, Ernie McCracken does the same. The crowd’s reaction is genuine and is actually for Murray. Woody Harrelson, on the other hand, was a terrible bowler and according to the Farrelly brothers maybe got one or two strikes throughout the filming.

12 – Little Miss Sunshine (2006)

Steve Carell, at the time he was cast for Little Miss Sunshine (2006), was a relative unknown in Hollywood. According to an article in Entertainment Weekly, the producers of the film worried that he wasn’t a big enough star and didn’t have much acting experience. However, between the time the film was shot in the summer of 2005 and its release in the summer of 2006, Carell became a huge success as the star of the high-grossing film The 40-Year-Old Virgin (2005) in August 2005 and the leading character of the popular NBC Emmy-winning television series The Office (2005), which premiered in March 2005 and for which Carell won a Golden Globe in 2006 for best lead actor in a comedy television series. In the span of just one year, Carell had become such a star that the producers had gone from protesting his casting to tapping him to do prominent promotion for the film. Bill Murray was the original choice to play Frank. The second choice was Robin Williams.  Thomas Haden Church turned down the role of Richard Hoover, a decision he said he later regretted.

11 – It’s a Mad Mad Mad Mad World (1963)

Stanley Kramer, who was known for doing serious films like Inherit the Wind (1960) and Judgment at Nuremberg (1961), set out to make this the ultimate comedy film. It became well known that Stanley Kramer was casting nearly every comedy performer he could think of. Some famous stars actually contacted Kramer to volunteer for the project, or to inquire as to why they had not been contacted. When this film was made there were about 100 stunt performers in the US. About 80 of them worked on this film. When the cast first assembled for a meeting with director Stanley Kramer, they were shown the stunts and second unit footage that had already been shot. Buddy Hackett was so impressed that he went to Kramer and asked, “What do you need US for?”

The film was so crammed with action that each leading actor was given two scripts: one for the dialogue and one for physical comedy. For one particular stunt, a billboard that the twin-engine Beechcraft flies through was made of thin balsa wood, except for a thicker frame for support. Stunt pilot Frank Tallman had to fly the aircraft directly through the center of the billboard or the thicker frame would shear off a wing. The billboard was located in Irvine, at what is now the intersection of Interstate 405 and Hwy. 133 (Laguna Canyon), near Lion Country Safari, just east of John Wayne Airport. They had practiced with paper signs but used balsa wood for the actual movie stunt. The wood stopped one engine and the other was sputtering enough that the plane barely made it back to John Wayne Airport.

10 – Midnight Run (1988)

The boxcar scene where Jack Walsh (Robert De Niro) and John Mardukas (Charles Grodin) discuss whether or not they could ever be friends, was almost entirely improvised on-set. As regards Grodin’s famous, “You ever had sex with an animal, Jack?” line, he was told by Director Martin Brest to come up with something that was guaranteed to make even Robert De Niro laugh. The scene where John Mardukas (Charles Grodin) falls off a cliff was shot in the Salt River Canyon in eastern Arizona. However, the conclusion of the scene, the shots of Mardukas and Jack Walsh (Robert De Niro) crashing through the river rapids, was shot in New Zealand, because the water was too cold in Arizona. I have to pause here…too cold. In Arizona.

9 – Paper Moon (1973)

I talk about this movie in a post about Madeline Kahn, you can read it here: KAHN  Ryan O’Neal and daughter Tatum O’Neal are both excellent as well as Madeline Kahn, in this. Tatum O’Neal was 10 years old when she won the Academy Award for Best Supporting Actress for her performance in this movie, making her the youngest person ever to win an Oscar in a competitive category. As of 2018, she still holds this record. She was four years younger than her rival nominee, Linda Blair, in The Exorcist (1973). Some Hollywood insiders suspected that Tatum O’Neal’s performance was “manufactured” by Peter Bogdanovich. It was revealed that the director had gone to great lengths, sometimes requiring as many as fifty takes of some of her scenes, in order to capture the “effortless” natural quality for which Tatum was critically praised. Either way, Bogdanovich maintained later that working with the young actress was “one of the most miserable experiences” of his life.

Prior to finalizing casting, Peter Bogdanovich says he met with Ryan O’Neal and Tatum O’Neal at their Malibu home. When Ryan invited Bogdanovich to start an exercise regimen of running on the beach, Tatum countered he wasn’t the type. When she explained to Bogdanovich she said that because he wouldn’t take his shoes or shirt off, he told Ryan, “She’ll do.” Peter Bogdanovich didn’t think the movie would make much money or would be very successful. He certainly didn’t think Tatum O’Neal would win the Oscar.  The film spawned an unsuccessful TV series Paper Moon (1974) starring Jodie Foster.

8 – Cannonball Run (1981)

I talk about Cannonball run at length at a post you can read HERE. In one of the earlier scenes in the movie, J.J. McClure (Burt Reynolds) said “Could get a black Trans Am”, and then answers himself, “Naw, that’s been done.” This is a reference to Smokey and the Bandit (1977) and Smokey and the Bandit II (1980), which starred Reynolds, and was directed by Hal Needham, who directed this film. DeLuise co-starred with Reynolds in Smokey and the Bandit II (1980).

7 – The Adventures of Priscilla, Queen of the Desert (1994)

According to director Stephan Elliott, he took the three leads out in drag prior to the beginning of filming. None of them were recognized: Guy Pearce took the opportunity to be outrageously rude, Terence Stamp eventually forgot he was in drag and started hitting on girls, and Hugo Weaving got super-drunk and lay under a table for hours, tapping his finger in time to the music. This last detail was incorporated into the film in the hotel room scene.

6 – Dumb and Dumber (1994)

Harry and Lloyd are named after the (silent) comedy star Harold Lloyd. The feature film debut for Peter Farrelly and Bobby Farrelly. They said years later that the main reason they got the job was that Jim Carrey’s breakthrough film role in Ace Ventura: Pet Detective (1994) had been directed by someone who had never done a feature film before (Tom Shadyac) and after a positive first meeting with the Farrellys, Carrey decided to give them the job in hopes of replicating that success. According to the Farrelly brothers, Jeff Daniels wasn’t wanted for the film, but Jim Carrey wanted him in it. In order to ensure a no from him, they offered Daniels $50,000 for the role. He accepted without any hesitation nor did he attempt to negotiate, despite insistence from his agent the film would “kill his career.” By 1994, the film was Daniels’ most successful.

5 – It Happened One Night (1934)It Happened One Night (1934) became the first film to perform a “clean sweep” of the top five Academy Award categories, known as the Oscar “grand slam”: Best Picture, Best Director, Best Actor, Best Actress, and Best Screenplay. This feat would later be duplicated by One Flew Over the Cuckoo’s Nest (1975) in 1976 and The Silence of the Lambs (1991) in 1992. However, It Happened One Night is the only one not nominated in any other category. According to Frank Capra in an interview with Richard Schickel for “The Men Who Made the Movies”, “We made the picture really quickly–four weeks. We stumbled through it, we laughed our way through it. And this goes to show you how much luck and timing and being in the right place at the right time means in show business; how sometimes no preparation at all is better than all the preparation in the world, and sometimes you need great preparation, but you can never out-guess this thing called creativity. It happens in the strangest places and under the strangest of circumstances. I didn’t care much for the picture, ] it turned out to be ‘It Happened One Night’.” Is often credited as the very first screwball comedy.

4 – Tommy Boy (1995)Rob Lowe played the supporting role of Tommy’s stepbrother and is uncredited. The reason for this is because Rob was contractually obligated to Stephen King’s The Stand (1994) at the time, so he took the part simply as a favor for friend Chris Farley. According to David Spade, he and Chris Farley got into a physical altercation on the set. Spade had gone out for a drink with Rob Lowe the night before. Farley had become very jealous and angrily repeated: “How’s Rob Lowe?”. David got so fed up with Chris hounding him on the subject that he threw his Diet Coke on him, to which Chris responded by throwing David into a wall and down the stairs. After the fight, Spade walked off the set and refused to continue filming. The pair would sometimes go for hours without talking to each other, talk to each other through the director, etc.

3 – The Blues Brothers (1980)During filming one of the night scenes, John Belushi disappeared and could not be located. Dan Aykroyd looked around and saw a single house with its lights on. He went to the house and was prepared to identify himself, the movie, and that they were looking for Belushi. Before he could, the homeowner looked at him, smiled and said, “You’re here for John Belushi, aren’t you?” The homeowner then told them Belushi had entered their house, asked if he could have a glass of milk and a sandwich, and then crashed on their couch. Situations like this prompted Aykroyd to affectionately dub Belushi as “America’s Guest”. John Candy orders three orange whips. This line was not scripted; Candy just improvised. While also a cocktail, Orange Whip provided refreshments for the crew, and Costumer Sue Dugan was daughter of the Director of Sales for Orange Whip, Kenny Dugan, who asked the brand be mentioned in the film.

2 – Smokey and the Bandit (1977)A majority of the lines and quotes spoken by Jackie Gleason character, Sheriff Buford T. Justice were improvised. Jackie Gleason reportedly modeled his character, Sheriff Buford T. Justice, after Burt Reynolds’ description of his father, a Florida police officer and Chief of Police. Among the character traits that came from this was the use of “sumbitch”, a colloquial pronunciation of “son of a bitch”. Jackie Gleason said the cafe scene with himself and Burt Reynolds was not in the original story, it was Gleason’s idea. Adding the Junior Justice character was Jackie Gleason’s idea. “I can’t be in the car alone,” Gleason said. “Put someone in there with me to play off of.”

Hal Needham was better known in the film industry as a stuntman and had great difficulty in getting any producers interested in this project. Only when his close friend Burt Reynolds agreed to star in the film did he manage to gain studio attention. Hal Needham asked Jerry Reed to write a theme song for the film. A couple of hours later, Reed presented “East Bound and Down” to Needham. With an acoustic guitar, Reed started to play it and Needham immediately stopped him. Thinking Needham didn’t like it, Reed offered to re-write the song. To which Needham replied: “If you change one note, I’ll kill you!” The song went on to become one of Reed’s biggest hits.

1 – Planes, Trains & Automobiles (1987)John Hughes, in an interview on the “Those Aren’t Pillows” DVD, said he was inspired to write the film’s story after an actual flight from New York to Chicago he was on, was diverted to Wichita, Kansas, thus taking him five days to get home. John Hughes wrote the first draft of the screenplay in three days. His average writing time for a screenplay in those days was about three to five days with twenty-some re-writes. Steve Martin was convinced to join the production after favoring two scenes he had read from the script; the seat adjustment-scene in the car, and the F-word tirade at the car rental desk. John Candy and Steve Martin’s favorite film that they have made. Although John Hughes was in a bad mood throughout the filming, as his life was falling apart, John Candy and Steve Martin had a great time together during production.