Dynamic Watchlist Hub: Apr 19, 2026

10 Best Movies Like Upstart

If you loved Upstart, 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 Upstart.

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#1
The Distinguished Gentleman

The Distinguished Gentleman

1992★ 6.0

Why watch this? A perfect follow-up to Upstart for fans of Comedy. It captures a similar light-hearted atmosphere.

A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, th...

#2
Pretty Woman

Pretty Woman

1990★ 7.4

Why watch this? A perfect follow-up to Upstart for fans of Romance. It captures a similar light-hearted atmosphere.

Vivian is a carefree, streetwise diamond in the rough when she meets sophisticated billionaire Edward in a chance encounter that turns into a week-long business arrangement. But Vi...

#3
The Disaster Artist

The Disaster Artist

2017★ 7.1

Why watch this? A perfect follow-up to Upstart for fans of Comedy. It captures a similar light-hearted atmosphere.

An aspiring actor in Hollywood meets an enigmatic stranger by the name of Tommy Wiseau, the meeting leads the actor down a path nobody could have predicted; creating the worst movi...

#4
American Dreamer

American Dreamer

2022★ 5.8

Why watch this? A perfect follow-up to Upstart for fans of Comedy. It captures a similar light-hearted atmosphere.

In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy...

#5
The Million Pound Note

The Million Pound Note

1954★ 6.8

Why watch this? A perfect follow-up to Upstart for fans of Comedy. It captures a similar light-hearted atmosphere.

An impoverished American sailor is fortunate enough to be passing the house of two rich gentlemen who have conceived the crazy idea of distributing a note worth one million pounds....

#6
The Lady Eve

The Lady Eve

1941★ 7.2

Why watch this? A perfect follow-up to Upstart for fans of Comedy. It captures a similar light-hearted atmosphere.

It's no accident when wealthy Charles falls for Jean. Jean is a con artist with her sights set on Charles' fortune. Matters complicate when Jean starts falling for her mark. When C...

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