10 Great 1990s Comedy Movie Classics You Probably Haven’t Seen

6. What About Bob? (1991)

There’s no doubt if Bill Murray is in a comedy, most likely it’s going to be funny. This one is no exception. Murray delivers his most underrated performance as an unstable and needy man who struggles with the easy things in life. The only sanctuary comes from his therapist who is going away with his family for a month. Murray can’t handle life without him for that long, so he goes to find him and befriends his family. Co-starring the whacky Richard Dreyfuss as his therapist who starts to lose his mind because Murray intervenes on his family vacation. Julie Haggerty of Airplane fame plays Dreyfuss’ wife.

Frank Oz is in the director’s chair for this one. While millions would recognize Oz as the voice of several Sesame Street and Muppet characters, he’s also an accomplished comedy director. His credits include Little Shop Of Horrors, Dirty Rotten Scoundrels, In & Out and Bowfinger. All his films feature the funniest actors of all time – Rick Moranis, Steve Martin, Kevin Kline and Eddie Murphy. And of course, Bill Murray.


7. Tin Cup (1996)

Kevin Costner is not associated with many comedies which is the reason this film is so charming. He has a knack for comedy which he clearly shows here. To add to the funny, Cheech Marin brings hilarious moments to the equation. It’s a story about the least funny sport there is – golf. While Adam Sandler was able to bring an over-the-top hilarity to the sport in Happy Gilmore in the same year, Costner tones it down to a realistic type of humor. The incredibly charming Rene Russo brings heart to the film and keeps up with the comedy herself.

Costner reteams with Director Ron Shelton after their 1988 baseball comedy, Bull Durham. Shelton has a filmography filled with quality sports films: The Best Of Times, White Men Can’t Jump, Blue Chips and Cobb. Sports films usually have exciting climaxes and Tin Cup has one of the best which makes it a must see.


8. Taking Care Of Business (1990)

The unusual pairing of Jim Belushi and Charles Grodin makes this movie enjoyable. Belushi escapes from prison for the most logical reason one would – to go to the World Series. Grodin is a rich man who can’t stop thinking about work. Belushi takes on Grodin’s identity and the laughs never stop. He’s carefree as he reaps in the rewards of Grodin’s life including his luxurious house and a gorgeous woman he meets. Belushi is underrated as a comedic actor, but definitely delivers here.

The film was directed by Arthur Hiller who has his share of classic comedies with some of the most famous comedic actors: Plaza Suite (Walter Matthau), Silver Streak (Gene Wilder and Richard Pryor) and The In-Laws (Alan Arkin and Peter Falk). This was the first film from screenwriter Jeffrey Abrams who would later become the famed showrunner and filmmaker J.J. Abrams.


9. Jingle All The Way (1996)

Arnold Schwarzenegger scored big with his first two comedies: Twins and Kindergarten Cop. Later his comedies got sillier with Junior and then Jingle All The Way. In Jingle, he’s a busy dad who rushes through stores during the holiday season to find a hard-to-get toy for his son. Schwarzenegger jumps into the role headfirst as he would in any action film. The only difference here is he splashes the movie with laughs.

Finding the toy is hard enough, but every Arnold movie needs a villain. Here it’s the hilarious stand-up comedian Sinbad. They go to battle to find the toy – comedically of course. The amazing Phill Hartman shows up and delivers as always. Schwarzenegger shows a fun side of himself that he rarely shows in his movies. This is probably the role that’s closest to who he really is because he’s very funny in real life. That side of him is what makes this film so much fun and required viewing for any Arnold fan.


10. Necessary Roughness (1991)

Not to be confused with the USA Network Series, this movie is about college football. In the style of the 1989 movie Major League, the Fightin’ Armadillos of Texas State University are hopeless. They recruit a 34-year-old quarterback played by the incomparable Scott Bakula. The coaches are perfectly cast – legendary actors Robert Loggia and Hector Elizondo. On the offensive and defensive lines – Sinbad, Jason Bateman and other hopeless players including a militant karate guy. The kicker that’s recruited is the prettiest player on the team – Kathy Ireland. The always fun to hate Larry Miller tries to ruin the team as the Dean of the college.

Lastly, doing some hilarious commentary – Rob Schneider. All the players fill the field with lots of laughs. Watch for some hilarious cameos by Dick Butkus, Evander Holyfield and other famous sports figures as the scrimmage team. Even though the film is in fact silly, the score is amazing. No, not score of the game. The music composed by Bill Conti who brings out the excitement of the movie. With Conti’s second film on this list, it goes to show that comedies benefit from strong music as they balance the humor so well.