The Most Underrated Comedies Of The 1990s

List Rules
Vote up the '90s comedies that are low-key classics.

Comedies reigned supreme in the escapism of 1990s entertainment, though a great number of underrated films were either neglected in their time or have been lost in the conversation ever since. There were a variety of different subgenres of comedies popularized in the 1990s. A sudden surge in romantic comedies followed the success of When Harry Met Sally... at the tail end of the 1980s, leading to the success of Pretty Woman, Sleepless in Seattle, and countless others in the 1990s. Slapstick had a return with the immature comedies featuring Jim Carrey, who would also be the first actor to receive a $20 million paycheck for a film in the 1990s. Even sex comedies had a comeback at the end of the decade, following the blockbuster success of American Pie.

Every decade has underrated comedies, though the 1990s seem especially full of them. For every unforgettable comedic release in the '90s, there are multiple overlooked gems. Sometimes films were lost in the shuffle of too many similar releases, never receiving the attention they deserve, while in other cases, they have been forgotten over time. Either way, the 1990s comedies included here are deserving of further consideration.

  • Grosse Pointe Blank is a dark comedy about a hit man who returns to his hometown for a high school reunion, only to have it interrupted by work. The film had a great premise that was made fantastic by perfect casting. John Cusack stars as Martin Blank, the professional killer returning to his hometown of Grosse Pointe, MI. The film’s dialogue matches the cleverness of the title with quick banter, sometimes between John and his real-life sister Joan Cusack, who appears as his handler in the film.

    Minnie Driver is also fantastic as a long-lost high school sweetheart, and Dan Aykroyd plays against type as a rival assassin. Blending action with humor can be a difficult task, but Grosse Pointe Blank handles it with ease. There are many Cusack films deserving of revisiting, and this is at the top of the list.

  • 2
    997 VOTES

    What About Bob? is a dark comedy that plays like a lighthearted take on Cape Fear. When egotistical psychotherapist Dr. Leo Marvin (Richard Dreyfuss) has a difficult new patient, Bob Wiley (Bill Murray), pawned off on him from a fellow therapist, he gives the unstable man a copy of his recently published book, Baby Steps. Wiley takes those baby steps in the direction of his new doctor’s family vacation home, much to Marvin’s irritation.

    The fact that Murray actually annoyed Dreyfuss on-set may be why the dynamic between the two is so believable. What About Bob? may not be as popular as some of Murray’s other '90s comedies, but it is every bit as funny. And the fact that Dr. Marvin uses hand puppets as a therapeutic tool is humorous on multiple levels, given that the director is legendary puppeteer Frank Oz.

  • 3
    719 VOTES

    After the massive success of Swingers, director Doug Liman was hired to direct the crime comedy Go. The ensemble film involves several characters and storylines that intersect over the course of one evening. Drug sales carried out by amateurs go horribly wrong, and a supermarket employee (Sarah Polley) gets dragged into a sting operation fronted by soap opera actors (Scott Wolf and Jay Mohr).

    With a storyline involving drug-fueled raves and a screenplay attempting to imitate Quentin Tarantino’s signature dialogue and non-chronological storytelling, Go is a distinctly '90s film. It was dismissed by some for these reasons, but has built a solid cult following over the years, thanks to the sharp writing and cast of charismatic actors that includes Katie Holmes, Timothy Olyphant, William Fichtner, and Taye Diggs. Melissa McCarthy also had her feature-film debut with a small supporting role.

  • 4
    765 VOTES

    Often described as a psychological romantic comedy, Benny & Joon is a sweet love story between two extremely eccentric individuals. Benny (Aidan Quinn) cares for his mentally unstable sister Joon (Mary Stuart Masterson), but it prevents him from having a life of his own until the enigmatic Sam (Johnny Depp) enters their lives. After Benny wins Sam in a poker game, the film-obsessed man moves in with the siblings and provides Joon with a relationship that challenges her to grow.

    Much of the film’s charm comes from Depp’s performance, which is filled with slapstick comedy routines directly lifted from the comedy of Buster Keaton, Charlie Chaplin, and Harold Lloyd. Although Benny & Joon was a surprise success given the untraditional narrative, it often gets lost amidst the countless other romantic comedies of the decade.