Movies Like Richard Lewis: I'm Doomed

If you liked Richard Lewis: I'm Doomed (1990), a comedy movie directed by Bruce Gowers, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
2
Cadet Kelly (2002)
★ 6.2/10Also comedy
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.
3
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
4
The Pink Panther Strikes Again (1976)
★ 6.9/10Also comedy
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
5
The Mouse That Roared (1959)
★ 6.4/10Also comedy
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
6
Hollywood or Bust (1956)
★ 6.2/10Also comedy
The last movie with Jerry Lewis and Dean Martin together, is a satire of the life in Hollywood. Steve Wiley is a deceiver who cheats Malcolm Smith when he wins a car, claiming that he won it too. Trying to steal the…
7
Gabriel Iglesias: Aloha Fluffy (2013)
★ 7.1/10Also comedy
ALOHAAAAA! Internationally acclaimed comedian, Gabriel Iglesias, returns to Comedy Central with his latest stand-up special taped at Honolulu’s Hawaii Theatre Center. Watch as Fluffy brings the house down yet again in…
8
Malibu Rescue: The Next Wave (2020)
★ 6.2/10Also comedy
It’s summer again, and everyone’s favorite Junior Rescuers, The Flounders, are back at Tower 2. With the International Junior Rescue Championships headed to Southern California, the eyes of the entire planet are on…
9
Perfect Day (1929)
★ 7/10Also comedy
Two families embark on a pleasant Sunday picnic but manage to run into a variety of issues with their temperamental automobile. Each incident requires repeated exits and reboardings by Laurel, Hardy, their wives and…
10
Grown Ups (2010)
★ 6.4/10Also comedy
After their high school basketball coach passes away, five good friends and former teammates reunite for a Fourth of July holiday weekend.
11
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
12
Beverly Hills Chihuahua 2 (2011)
★ 5.9/10Also comedy
Puppy mayhem turns the lives of newlywed Chihuahua parents Papi and Chloe upside down when their rambunctious, mischievous puppies present one challenge after another. But when their human owners end up in trouble, the…
13
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
14
Adventures in Public School (2018)
★ 6.3/10Also comedy
A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.
15
Bowfinger (1999)
★ 6.2/10Also comedy
On the verge of bankruptcy and desperate for his big break, aspiring filmmaker Bobby Bowfinger concocts a crazy plan to make his ultimate dream movie. Rallying a ragtag team that includes a starry-eyed ingenue, a…
16
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
17
The Naked Gun 2½: The Smell of Fear (1991)
★ 6.8/10Also comedy
Bumbling lieutenant Frank Drebin is out to foil the big boys in the energy industry, who intend to suppress technology that will put them out of business.
18
Godspell (1973)
★ 6.7/10Also comedy
In modern-day New York City, John the Baptist calls out to a group of young men and women to learn from the teachings of Jesus. Through song and dance, they relive Christ's crucifixion.
19
Tommy Boy (1995)
★ 6.8/10Also comedy
To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.
20
A Song Is Born (1948)
★ 6.5/10Also comedy
The story of seven scholars in search of an expert to teach them about swing music. They seem to have found the perfect candidate in winsome nightclub singer Honey Swanson. But Honey's gangster boyfriend doesn't want…