15 Best Comedies on Showtime

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If you’ve been itching for a good movie with a few laughs and you have access to Showtime’s amazing selection of films, you’re at the right place! Read on to know the best of the best on Showtime.

15 of the funniest comedies available on Showtime – 2020 update

  1. The Waterboy
  2. Mean Girls
  3. Paul Blart: Mall Cop
  4. Fever Pitch
  5. Fright Night
  6. Extra Ordinary
  7. The House of Tomorrow
  8. Risky Business
  9. The Upside
  10. Green Book
  11. Spaceballs
  12. The Truman Show
  13. 50/50
  14. Pretty in Pink
  15. The House with a Clock in its Walls

1. Waterboy

IMDBRotten TomatoesWhere to Watch
6.135Showtime

Producing big smiles and belly laughs, The Waterboy follows Bobby Boucher (played by Adam Sandler) who is a waterboy for a struggling team before the coach discovers Bobby’s hidden talent as a tackler. Follow Sandler’s Bobby as he discovers that there is more to life outside of his bedroom.

Though The Waterboy isn’t a critical success, it has become a cult classic over the years. It’s definitely up there with some of the best Adam Sandler films. Though it isn’t the comedy I typically go for, it is a fun watch that should be watched at one point in your life.

Showtime is the only screening service that offers The Waterboy, but you can rent or buy it on services like Amazon, Apple, Youtube, and others. It’s also available through cable or services like FuboTV if you have Showtime through them.

2. Mean Girls

IMDBRotten TomatoesWhere to Watch
784Showtime

Mean Girls is a fun coming-of-age story about Lindsay Lohan’s Cady Heron discovering how vicious high school girls can be. Since she was educated by her parents in Africa, she is unfamiliar with the atmosphere of a public school. She quickly finds out though when she gets involved with the mean girls’ clique when she goes to a public high school for the first time.

A pop-culture phenomenon is an understatement for this film. The popularity even leads to a sequel and very successful Broadway musical. Though the cast has other notable work, they are commonly known for their role in this movie.

This film is one of the most recognizable films for anyone born in the late 90s or early 2000s. This movie has defined childhood for many, and for that reason, everyone should watch it at least once.

Mean Girls is only available through FuboTV, but along with buying or renting it anywhere that offers that, it is also available if you have Showtime through cable or services like FuboTV. 

3. Paul Blart: Mall Cop

IMDBRotten TomatoesWhere to Watch
5.233Showtime

In typical Kevin James fashion, he puts on an electric performance as a mall cop named Paul Blart that is forced to use his knowledge of the mall to his advantage when Santa’s little helpers take hostages including Blart’s daughter and girlfriend. James is able to portray a comedic character who will steal all of the hearts of anyone who watches.

Though not as successful as Adam Sandler, Kevin James had a great deal of success for comedies in the 2000s. Paul Blart: Mall Cop certainly isn’t a masterpiece, but with Kevin James’ perfect comedic timing, it is enjoyable nonetheless.

Paul Blart: Mall Cop is only available through Showtime. If you have cable which offers Showtime, you can also watch it there.

4. Fever Pitch (2005 US)

IMDBRotten TomatoesWhere to Watch
6.265Showtime

As a businesswoman, Barrymore’s Lindsey doesn’t seem like the obvious fit for Fallon’s Ben. However, they still give it a chance as they feel a deep connection. It goes well until Lindsey realizes that Ben’s obsession over baseball might be a bit much for her. This can be a fun movie to laugh at for any couple that has found themselves in a similar situation.

Fittingly, this rom-com is a great watch when you’re wanting to wind down from watching an intense baseball game with your favorite team. Jimmy Fallon’s screen presence and Drew Barrymore’s charisma will make you feel right at home with this sports rom-com about an unlikely couple working on their differences. Though not a home-run, Fever Pitch is a fun watch.

Showtime is the only streaming service that offers Fever Pitch, but if you have Showtime through cable, you can watch it there along with services like FuboTV.

5. Fright Night

IMDBRotten TomatoesWhere to Watch
6.372Showtime

This 2011 remake of the 1985 cult classic brings enough horror and comedy for you and all of your friends. You’re in for a ride during this comedic vampire journey where Anton Yelchin’s Charley Brewster goes to David Tennant’s Peter Vincent for supernatural help when he discovers that his new neighbor, Jerry, is a vampire which is played wonderfully by Colin Farrell.

Though I would have loved to see this movie lean into the comedy a bit more, I did enjoy what I saw. Loving this kind of film, it definitely interested me throughout. Excellent performances from familiar faces like Colin Farrell and Toni Collette is enough to make you want to watch this film.

Fright Night is available through Showtime’s app or any other way you access Showtime such as Amazon add-ons, cable, or Hulu add-ons

6. Extra Ordinary

IMDBRotten TomatoesWhere to Watch
6.498Showtime

This movie follows Maeve Higgins’ Rose as an ex ghost hunter who is reluctantly led back into the field afraid of a repeat of the tragic accident that caused her father’s death. By using tear-inducing jokes and the actors’ charisma, you will be happy to follow Rose’ on her journey of self-discovery through helping a new friend save his daughter.

If you’re looking for a horror-comedy double feature, Extra Ordinary would be a great follow-up after Fright Night. By leaning into the ridiculous comedy a bit more than Fright Night, this one will be a perfect end to your night. You will be laughing for hours after the ending. 

Personally, this is one of the funniest films out of the entire list. With a witty script that is comparable to some of the best comedies, it won’t be a disappointment to many that sit down to watch it.

Extra Ordinary is available through Showtime along with cable, buy or rent, add-ons, and library services like Hoopla and Kanopy.

7. The House of Tomorrow

IMDBRotten TomatoesWhere to Watch
6.275Showtime

An unoriginal but endearing story of friendship perfectly describes The House of Tomorrow. By befriending Alex Wolff’s Jared Whitcomb, Asa Butterfield’s Sebastian Prendergast discovers his place in the world isn’t what he originally thought. He’s put through challenges with his overbearing grandmother who means well and Whitcomb’s unfortunate health issues, but he bounces back in this heartfelt comedy.

As this is the type of story I enjoy, it was certainly a good watch. It had its problems, but Asa Butterfield’s chemistry with Alex Wolff was enough to win me over. Since it is a drama along with being a comedy, you may need to bring along some tissues just in case.

The emotional moments, both sad and funny, are due to Alex Wolff’s witty performance. It’s nice to see him lend his talent to smaller films like this one when he has now went on to be in bigger films like Hereditary and the recent Jumanji films. He has certainly grown as an actor since his Nickelodeon days.

Along with Showtime, The House of Tomorrow is available through cable, buy or rent, add-ons, and Hoopla.

8. Risky Business

IMDBRotten TomatoesWhere to Watch
6.892Showtime

Risky Business is a cult classic that follows Tom Cruise’s Joel Goodsen who decides to stop being the good kid when he has left home alone for a few days. By doing so, he gets into some risky business, hence the name, and he has to find a way out of it.

Much like a similar film called Ferris Bueller’s Day Off, Risky Business has managed to get quite the following years after its release. It shows teen angst in a sharp manner getting many laughs out of the audience. Its considered the film with one of Cruise’s best early performances, and after you watch it, you will see why.

Showtime is the main service to offer Risky Business. Along with buying or renting it, you can access it through FuboTV or add-ons through Amazon or Hulu.

9. The Upside

IMDBRotten TomatoesWhere to Watch
6.942Showtime

The Upside is a remake of the 2011 French comedy The Intouchables which should never be compared to the original as that just sets it up for failure. However, the charming story of friendship between two unlikely pals played by Kevin Hart and Bryan Cranston will still make you smile.

Shown through the Rotten Tomatoes score, this film isn’t without its critics. Rotten Tomatoes describes it as “preachy, manipulative, and frustratingly cliched” which may steer you away from this film. However, with a much higher audience score (82%), this film has watchers who praise it for its charming story about friendship.

One critique that is worth mentioning is how a friendship between a white person and Black person is betrayed. In fact, Variety published an interesting review in which it called out the movie for this poor portrayal saying – that it seems outdated.

The Upside is a little less accessible than the others as the only way to access it online other than where you watch Showtime is to buy it through Amazon and Microsoft.

10. Green Book

IMDBRotten TomatoesWhere to Watch
8.278Showtime

Green Book follows Dr. Don Shirley (played by Mahershala Ali), a pianist, who goes to Viggo Mortensen’s Tony Lip for assistance in driving and protecting him during his concert tour in the deep South. Considering the location of the tour, they are forced to tackle the conversation of racism and segregation which was very prominent in the 60s which is when this movie takes place.

With its similarities to The Upside, Green Book would be a great film to watch in conjunction with The Upside. With both tackling racism through an unlikely friendship, you’ll have a lot of fun comparing the two in terms of how they represent certain parts of this very complex but charming story.

To show its credibility, it is worth mentioning that Green Book went on to win 3 Oscars out of 5 nominations including best motion picture and best original screenplay at The Oscars. It went even further with the wins and nominations with Golden Globes where it also won 3 out of 5 nominations including best screenplay and best motion picture.

Though Green Book and The Upside do share some similarities, they do not share similarities with accessibility. Green Book is available through anywhere you watch Showtime along with FuboTV and renting or buying.

11. Spaceballs

IMDBRotten TomatoesWhere to Watch
7.158Showtime
Netflix

Spaceballs is a comedic take on Star Wars which is a very well-known franchise. Though Star Wars isn’t known to be comedic, Spaceballs does all it can to get laughs out of its audience. In most cases, it actually succeeds with out-of-this-world jokes and plenty innuendos that shouldn’t be viewed by the innocent eye.

With an 83% audience score on Rotten Tomatoes compared to the 58% critics score, it’s obvious that this movie was taken too seriously by many critics. This is a fun movie that I’ve gotten many laughs out of, and I know many others who watch this film for a good laugh.

Spaceballs might be one of the most accessible on this list as it can be watched on Showtime and Netflix. Along with those two, it can be watched on FuboTV and Hoopla along with renting or buying wherever you choose to do so.

12. The Truman Show

IMDBRotten TomatoesWhere to Watch
8.195Showtime

The Truman Show is a thought-provoking comedy that follows Jim Carrey’s Truman Burbank as he discovers that his life is being used for a TV show. Much like Big Brother, he has no privacy as there are cameras throughout his house. As he figures out the truth, he has to decide what to do.

Much like others on this list, The Truman Show is a classic adored by many. It explores the exploitation of celebrities’ lives without permission to do so. This topic has become a bigger conversation as of late with celebrities getting fed up with the lack of privacy. With this said, this film is a great watch when you’re looking for something that’ll make you laugh while also making you think hard about the film.

A lot like the others, The Truman Show is only accessible through where you access Showtime along with FuboTV and buy/rent.

13. 50/50

IMDBRotten TomatoesWhere to Watch
7.693Showtime

50/50 follows Joseph Gordon Levitt’s Adam as he discovers that he has malignant tumors along his spine. His doctor gave him a 50/50 chance of surviving, and though he didn’t let it get him down, his friend Kyle (played by Seth Rogen) and his mother (played by Anjelica Huston) didn’t take the news well. Adam decides to start therapy which takes him on an interesting journey.

Though not as recognizable as some, 50/50 is still a critical darling that doesn’t get as much recognition as it should. According to reviewers, the standouts were most certainly the performances by Joseph Gordon Levitt along with its great balance between drama and jokes.

50/50 is only accessible through Showtime or anywhere you access Showtime along with FuboTV or buy/rent.

14. Pretty in Pink

IMDBRotten TomatoesWhere to Watch
6.875Showtime

Known for his charming screenwriting, John Hughes creates another coming-of-age story to charm whoever watches it. Molly Ringwald stars in her third John Hughes film in which she plays an outcast named Andie who goes through a journey of discovery with dating and her place at her school.

Pretty in Pink certainly has a place in many hearts, but it is unable to hold its own against other John Hughes film which could have to do with have a different director. However, John Hughes only writes the script for Home Alone, but we all know that movie. It still deserves recognition for a sweet comedic story that is just witty enough to work.

Along with Showtime, as usual, Pretty in Pink isn’t available anywhere else that isn’t the norm like buying or renting anywhere that offers the ability.

15. The House with a Clock in its Walls

IMDBRotten TomatoesWhere to Watch
6.066Showtime

The House with a Clock in its Walls is a family-friendly blend of humor and horror which stars Jack Black in the role of the oddball uncle named Jonathan Barnavelt. Jonathan’s nephew Lewis (played by Owen Vaccaro) visits his uncle’s house which is when he discovers that there is more to his uncle than just being an oddball with a house that makes weird tick noises.

This film certainly isn’t on the level of other Jack Black films like Jumanji: Welcome to the Jungle, but it is an enjoyable take on a story originally told by John Bellairs. According to most reviews, it’s not a movie that would win any awards or make a billion dollars at the box office, but it is still something that will leave you satisfied without feeling like your time was wasted.

The House with a Clock in its Walls is available through Showtime. Besides that, you can access it through FuboTV or however you usually buy movies online. However, it is not available for rent.

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