The 10 Most Rewatchable Comedy Movies of The 1990s

The 90s were a remarkable decade for cinema, and saw the emergence of many new directors, movie stars, and subgenres that would go on to influence the future of film. Few genres saw as radical of a shift as comedy did, with filmmakers and studios embracing different types of films that were more challenging. The rise of independent cinema also allowed for filmmakers to have more freedom in the types of stories they told.

While there are countless 90s comedies that are worth watching and deserve critical reflection, some stand out among the rest as being the most rewatchable due to the power of their stories and the irreverence of their humor. Here are ten of the most rewatchable comedies of the 1990s.


10. Get Shorty

Get Shorty satirizes Hollywood with razor sharp wit and explores how the brutal world of gangsters is not that different than the ruthless world of pitching films and wrangling movie stars. John Travolta gives one of the best performances of his career as Chili Palmer, a sly conman who ends up making his way to Hollywood in order to intimidate the studio producer Harry Zimm (Gene Hackman) into paying his debts. Chili’s realization that the shrewd skills he learned from a life of crime are perfectly suited for the movie business is uproariously hilarious, as is his budding romance with Rene Russo’s character, a second rate actress.

While it’s easy to appreciate Get Shorty on an initial viewing, there’s so much more to appreciate upon rewatch, specifically the performances. Travolta had just made a comeback the previous year with Pulp Fiction, and here he’s able to make another morally dubious character completely enthralling to watch. Hackman is also excellent, and gets to do a lot of physical comedy once Harry is brutally injured. There’s also a great supporting performance by Danny Devito as a Hollywood star who learns how to act like a criminal from Chili.

Get Shorty is also an interesting film to rewatch as it represents a very specific era in Hollywood filmmaking, in which original ideas and flashy movie stars were more important than franchises and established IP. Chili is able to get his movie idea made after he turns his life story into a convincing pitch to Harry, and by the end of the film, a version of that pitch is already being made into a feature film, with cameos from Harvey Keitel and Penny Marshall. Get Shorty explores the power of a charismatic storyteller in a meta way, but looking back at it 25 years later, it’s very much a sincere tribute to a different time for the industry.


9. Drop Dead Gorgeous

While it was maligned upon its initial release, Drop Dead Gorgeous became a sleeper cult classic in the early 21st Century, as its home video release drew the attention of many that had missed its initial theatrical run. As a mix of the teen rom-com, mockumentary, black comedy, and satire of small town America, Drop Dead Gorgeous paved a unique legacy that remains treasured today, with this year seeing its 20th anniversary and debut on streaming services.

A pseudo-documentary that follows the cutthroat nature of a teen beauty pageant in rural Minnesota, the film follows two of the main contestants: the charming, yet poor funeral home employee Amber (Kirsten Dunst) and the stuck up rich girl Becky (Denise Richards). While Dunst and Richards both do a great job at showing the cartoonish extremes of poverty and wealth, it’s the film’s eclectic ensemble that makes it feel lived in and authentic to how a massive media event would impact a small community. Actresses like Amy Adams, Brittany Murphy, Ellen Barkin, Kirstie Alley, Mindy Sterling, and Alison Janney all play absolute caricatures, each of which has a singular quirk that is used over and over as the media circus continues.

With its harsh satire regarding the over-sexualization of young women and frequent off color jokes at the expense of others, there’s no way Drop Dead Gorgeous could be made today, which makes it an interesting time capsule. It’s truly a film that intends to alienate its audience by being outrageously offensive, and is able to draw the viewers to Amber’s side as she’s faced with almost farcical injustice. Due to its provocative nature and the many actresses working outside of their comfort zone, Drop Dead Gorgeous is a great film to introduce to new audiences.


8. Swingers


While Jon Faverau and Doug Liman would both go on to direct huge budget action films, they began their career with the indie classic Swingers, which Faverau wrote and Liman directed. Swingers stands out as one of the best depictions of what it’s like to be an out of work actor, something Faverau based on his own experiences. It also feels completely genuine in its depiction of the L.A. dating scene and what it’s like to cope with a big breakup.

The line “Vegas, baby!” would go on to be an iconic one, and Swingers does an excellent job at making both Vegas and L.A. feel exciting and vibrant, allowing the characters to navigate between different parties and social circles with a carefree attitude. The terrific soundtrack, which includes a lot of swing classics from Frank Sinatra and Bobby Darin among others, also differentiates Swingers from other films about L.A.

Faverau and Vince Vaughn made for a perfect screen duo, as Vaughn’s uber confidence talking to women makes for a great contrast to Faverau, who’s stuck reminiscing upon his failed relationship. The script lets both characters develop in interesting ways, as Faverau finds a new partner that inspires him to stay in L.A., and Vaughn begins to learn that he’s not quite the womanizer he makes himself out to be. Ultimately, it’s the chemistry between the two and their genuine care for each other that makes Swingers rewatchable to this day.


7. Clerks

Clerks is arguably one of the most important films of the 90s, as it remains one of the standout examples of what could be achieved on a micro budget. Kevin Smith shot the film at the actual store he worked at for less than $30,000, and his success would go on to spawn many imitators. It also became the film in Smith’s View Askewniverse shared cinematic universe, which would go on to include Mallrats, Chasing Amy, Dogman, Jay and Silent Bob Strike Back, Clerks II, and the upcoming Jay and Silent Bob Remake.

As Clerks was made on such a small scale, it is rewatchable due to the great dialogue and characters. As a convenience store employee himself, Smith was able to make the discussions about life, relationships, and pop culture feel completely authentic, with two very relatable lead performances from Brian O’Halloran as the lead Dante and Jeff Anderson as the lazy Randal. Smith based Dante on himself, and is instantly able to get the audience on Dante’s side as he’s faced with constant setbacks and feels trapped in his boring, mundane job.

Clerks also saw the debut of the hilarious stoners Jay and Silent Bob; while these characters would go on to have starring roles in other films, their role in the first film is mostly a cameo, although Silent Bob gives the best monologue in the film when he explains to Dante that he should stay with his girlfriend Veronica. Compared to Smith’s later efforts, Clerks ends rather ambiguously and is often quite sad and meditative, as Dante questions his life choices. It’s a very unique debut that is worth rewatching over and over to appreciate how much of a game changer it was.


6. Groundhog Day


Groundhog Day has one of the greatest screenplays ever written, and perfectly uses a time loop to explore how a narcissistic pessimist can become a better person. It’s a philosophically rich text that shows how getting to relive key moments can be both a blessing and a curse, but it’s also a near perfect comedy. The running jokes regarding the elements of Phil Connors’s day that are repeated could easily become obnoxious if it wasn’t for Harold Ramis’s nuanced direction and screenplay.

Bill Murray has never been better than he is as Phil Connors; Murray excels at playing sardonic, snarky characters, and here he is able to deconstruct how lonely this cynical nature can be. None of the development for Phil is cheap, as it’s clear that the repetition of his day takes a toll on his patience and forces him to actually think about what is important in his life.

Many films have attempted to recreate the time loop formula that Groundhog Day perfected, but none are quite as endearing; when Phil confesses his love to his long standing producer Rita, there’s not a hint of irony from Murray. “I Got You Babe” will forever be linked to Groundhog Day, a film that is perfectly structured for repeated viewings.