Movies Like Hollywood Heartbreak

If you liked Hollywood Heartbreak (1988), a comedy and drama movie directed by Lance Dickson, 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
Don't Think Twice (2016)
★ 6.4/10Also comedy and drama
An improv group deals with several crises, including the loss of their lease and one member hitting the big time.
2
It Runs in the Family (2003)
★ 6/10Also comedy and drama
This is the story of a dysfunctional New York family, and their attempts to reconcile
3
The Good Half (2024)
★ 6.2/10Also comedy and drama
Renn Wheeland returns home to Cleveland for his mother's funeral. Once there, he forges new relationships while healing old ones, before confronting his problems and trying to face his grief.
4
Class Act (1992)
★ 6.3/10Also comedy and drama
Duncan is a genius straight A student, Blade is ajuvenile delinquent. But because of a mix up with their school records, everyone thinks each is the other one. Now, Duncan kind of likes the attention from being thought…
5
Wild Oats (2016)
★ 6.1/10Also comedy and drama
Everything changes for Eva when she receives an insurance settlement check accidentally made out for $5,000,000 instead of the expected $50,000. She and her best friend take the money and head out for the adventure of…
6
Chloe and Theo (2015)
★ 5.9/10Also comedy and drama
A young woman, Chloe, living by her wits on the streets of New York City, has a chance meeting with a wise Inuit Eskimo, Theo, who was sent to New York by his elders to provide a message to the people of the world – We…
7
Madea Goes to Jail - The Play (2006)
★ 7.5/10Also comedy and drama
Madea returns in another hilarious story in which she gets sent to the big house. But regardless of the circumstances, she gives her trademark advice and wisdom to her friends and family as they learn the importance of…
8
Better Living Through Chemistry (2014)
★ 5.9/10Also drama and comedy
A straight-laced pharmacist's uneventful life spirals out of control when he starts an affair with a trophy wife customer who takes him on a joyride involving sex, drugs and possibly murder.
9
Roll Bounce (2005)
★ 6.9/10Also comedy and drama
In the summer of 1978, a teenager and his group of friends face new challenges when their neighborhood roller-skating rink closes, forcing them to visit a different rink.
10
Hollywood Ending (2002)
★ 6.5/10Also comedy and drama
Woody Allen stars as Val Waxman, a two-time Oscar winner turned washed-up, neurotic director in desperate need of a comeback. When it comes, Waxman finds himself backed into a corner: Work for his ex-wife Ellie or…
11
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.
12
Afterlife of the Party (2021)
★ 6.7/10Also comedy and drama
A social butterfly who dies during her birthday week is given a second chance to right her wrongs on Earth.
13
Teen Spirit (2011)
★ 5.9/10Also drama and comedy
Amber, a mean popular girl who gets electrocuted and dies, is not allowed to enter into heaven unless she helps the least popular girl in school become Prom Queen within a week, but things do not go as planned.
14
Best Man Down (2012)
★ 6.6/10Also comedy and drama
A newlywed couple cancels their honeymoon and returns to the snowy Midwest to make the funeral arrangements for their best man, who died unexpectedly after their ceremony.
15
Little Big League (1994)
★ 6/10Also comedy
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
16
Swimming with Men (2018)
★ 6/10Also comedy and drama
A man who is suffering a mid-life crisis finds new meaning in his life as part of an all-male, middle-aged, amateur synchronised swimming team.
17
The Trip to Italy (2014)
★ 6.4/10Also comedy and drama
Years after their successful restaurant review tour of Northern England, Steve Coogan and Rob Brydon are commissioned for a new tour in Italy.
18
The Front (1976)
★ 7.1/10Also comedy and drama
A cashier poses as a writer for blacklisted talents to submit their work through, but the injustice around him pushes him to take a stand.
19
Swingers (1996)
★ 6.8/10Also comedy and drama
After 6 years together, Mike's girlfriend leaves him, so he travels to LA to be a star. Six months on, he's still not doing very well— so a few of his friends try to reconnect him to the social scene and hopefully help…
20
Chang Can Dunk (2023)
★ 6.7/10Also comedy and drama
Chang, a 16-year-old, Asian American, bets the high school basketball star that he can dunk by Homecoming. The bet leads 5' 8" Chang on a quest to learn to dunk—not only to impress his crush, Kristy, but to gain the…