Movies Like How to Succeed at Losing

If you liked How to Succeed at Losing (2023), a comedy movie directed by Rodrigo Triana, 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
No manches, Frida (2016)
★ 7.7/10Also comedy
After being released from prison, Zequi, a bank robber, sets out to recover money buried by his accomplice; but is horrified to learn that a high school gymnasium is now over the site where the loot is hidden.
2
Crazy Magical Mexico (2026)
★ 7.7/10Also comedy
A man finds the best motivation to secure and save his town: making an independent Mexican film.
3
The Key Game (2022)
★ 5.9/10Also comedy
Laura has been with Antonio all her life and, just when she begins to wonder if that is really the life she wants, Sergio and Siena cross paths in their lives. Sergio is a former high school classmate and Siena, his…
4
No manches, Frida 2: paraíso destruido (2019)
★ 7.9/10Also comedy
Zequi and Lucy are about to get married. Although he promises not to overdo it during the bachelor party, things get out of control.
5
Super Crazy (2018)
★ 6.7/10Also comedy
A 36-year-old meek woman realizes that there’s younger people trying to outpace her doing much less, so she makes a risky change by removing her filter.
6
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.
7
Valentina's Wedding (2018)
★ 6.5/10Also comedy
Valentina's seemingly idyllic life in the US is interrupted when planning a wedding means introducing her fiancé to her scandalous family in Mexico.
8
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
9
29th Street (1991)
★ 6.9/10Also comedy
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
10
Undercover Wedding Crashers (2021)
★ 5.9/10Also comedy
Geeky-looking Sebas is a surprisingly good classical musician. He’s also a complete unknown in the criminal underworld, and as a new newbie on the police force, that makes him the perfect man for a dangerous mission…
11
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
12
Jimmy Carr: Natural Born Killer (2024)
★ 6.4/10Also comedy
Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.
13
Old Dads (2023)
★ 6.2/10Also comedy
A cranky middle-aged dad and his two best friends find themselves out of step in a changing world of millennial CEOs and powerful preschool principals.
14
Me Time (2022)
★ 5.8/10Also comedy
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
15
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
16
Bendita Suegra (2023)
★ 8.4/10Also comedy
Andrea, a successful veterinarian who loves her job and is in a relationship with Lucio, an up-and-coming lawyer who grew up in the country. Lucio has some news for Andrea: his mother is turning 60 and is throwing a…
17
Double Pregnant (2019)
★ 7.3/10Also comedy
A woman gets pregnant with fraternal twins, one from her fiancé and the other from a former lover.
18
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
19
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
20
Louis C.K.: Oh My God (2013)
★ 7.6/10Also comedy
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for…