Dynamic Watchlist Hub: Apr 17, 2026

10 Best Movies Like How Not To Try Again

If you loved How Not To Try Again, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for How Not To Try Again.

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#1
Coyote Ugly

Coyote Ugly

2000★ 6.3

Why watch this? A perfect follow-up to How Not To Try Again for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and no...

#2
Fat Kid Rules The World

Fat Kid Rules The World

2012★ 6.7

Why watch this? A perfect follow-up to How Not To Try Again for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

A dropout comes to the aid of a chubby and suicidal high-school kid by recruiting him as the drummer for his upstart punk-rock band....

#3
Watching the Detectives

Watching the Detectives

2007★ 6.3

Why watch this? A perfect follow-up to How Not To Try Again for fans of Comedy. It captures a similar light-hearted atmosphere.

Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life fem...

#4
A Dog Year

A Dog Year

2009★ 6.2

Why watch this? A perfect follow-up to How Not To Try Again for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

Jon Katz is close to burnout. He's a writer with writer's block; his wife has left for her sister's because he's emotionally distant; he rarely answers his phone. A kennel sends hi...

#5
(Untitled)

(Untitled)

2009★ 6.4

Why watch this? A perfect follow-up to How Not To Try Again for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art....

#6
Amateur

Amateur

1994★ 6.1

Why watch this? A perfect follow-up to How Not To Try Again for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

A man wakes up in an alley, bleeding and with no memory of who he is. He stumbles into a coffee shop and is befriended by a charitable ex-nun who is failing in her attempts to writ...

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