Movies Like How to Successfully Fail in Hollywood

If you liked How to Successfully Fail in Hollywood (2023), a movie directed by C.M. Conway, 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
D.E.B.S. (2005)
★ 6.6/10
The star of a team of teenage crime fighters falls for the alluring villainess she must bring to justice.
2
Dinner in America (2022)
★ 7.8/10
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.
3
The Heavenly Kid (1985)
★ 6.6/10
After dying in a car crash, Bobby Fantana is forced to pay for his misdeeds by becoming someone's guardian angel. He reluctantly agrees to watch over awkward high schooler Lenny Barnes, teaching him how to be cool and…
4
Cinderella (2021)
★ 6.3/10
Cinderella, an orphaned girl with an evil stepmother, has big dreams and with the help of her Fabulous Godmother, she perseveres to make them come true.
5
Porno (2019)
★ 6/10
When a group of naive teens working at a movie theater in a small Christian town discover a mysterious film hidden in its basement, they unleash an alluring succubus who gives them a sex education…written in blood.
6
Lucky Them (2013)
★ 6/10
More interested in partying and flirting with young musicians than work, veteran rock journalist Ellie Klug has one last chance to prove her value to her magazine’s editor: a no-stone-unturned search to discover what…
7
The Object of My Affection (1998)
★ 5.8/10
A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.
8
¿Quieres ser mi hijo? (2023)
★ 8.4/10
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
9
Love Me Love Me (2026)
★ 6.1/10
After her brother's death, June moves to Milan for a fresh start, finding comfort in Will, the perfect honor student at her new international school. But when his troubled best friend James—hiding a dangerous life in…
10
Love Is in the Air (2023)
★ 6.2/10
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
11
The Half of It (2020)
★ 7.1/10
Shy, straight-A student Ellie is hired by sweet but inarticulate jock Paul, who needs help wooing the most popular girl in school. But their new and unlikely friendship gets tricky when Ellie discovers she has feelings…
12
My Sassy Girl (2008)
★ 6.8/10
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
13
The Kissing Booth 3 (2021)
★ 6.8/10
It's the summer before Elle heads to college, and she has a secret decision to make. Elle has been accepted into Harvard, where boyfriend Noah is matriculating, and also Berkeley, where her BFF Lee is headed and has to…
14
Heaven Can Wait (1978)
★ 6.7/10
Joe Pendleton is a quarterback preparing to lead his team to the superbowl when he is almost killed in an accident. An overanxious angel plucks him to heaven only to discover that he wasn't ready to die, and that his…
15
Green Lantern: Emerald Knights (2011)
★ 6.7/10
As the home planet of the Green Lantern Corps faces a battle with an ancient enemy, Hal Jordan prepares new recruit Arisia for the coming conflict by relating stories of the first Green Lantern and several of Hal's…
16
Private Valentine: Blonde & Dangerous (2008)
★ 6.2/10
When fluffy, bubble gum movie star Megan Valentine suddenly finds herself broke and humiliated in the public eye, she wanders from the wreckage of a car accident and witlessly enlists in the U.S. Army hoping in vain…
17
The Kissing Booth 2 (2020)
★ 7.6/10
With college decisions looming, Elle juggles her long-distance romance with Noah, changing relationship with bestie Lee and feelings for a new classmate.
18
Naomi and Ely's No Kiss List (2015)
★ 5.9/10
The bonds between Naomi and Ely are tested when they fall for the same guy.
19
Hollywood Dirt (2017)
★ 6.4/10
Hollywood arrives in force to Quincy, the small town where the secret Crown Cola billionaire's live. They want to film about the billionaire's and how they made their fortunes. Summer Jenkins, who was the town pariah…
20
Portal to Hell (2025)
★ 6/10
After a debt-collector finds a portal to hell in a washing machine at his local laundromat, he’s propositioned into feeding it sinners to save his neighbor’s soul, maybe even at the expense of his own.