Dynamic Watchlist Hub: Apr 18, 2026

10 Best Movies Like The Headstrong

If you loved The Headstrong, 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 The Headstrong.

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#1
Playing God

Playing God

2021★ 6.1

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

A brother and sister con-artist duo find themselves scamming a grieving billionaire by convincing him they can introduce him to God, face-to-face....

#2
Fun with Dick and Jane

Fun with Dick and Jane

1977★ 6.5

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

When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation....

#3
The Honey Pot

The Honey Pot

1967★ 6.4

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

In Venice, a millionaire hires an actor to help him prank three greedy exes into thinking he's dying and leaving his fortune to one of them....

#4
The Brothers Bloom

The Brothers Bloom

2008★ 6.5

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

The Brothers Bloom are the best con men in the world, swindling millionaires with complex scenarios of lust and intrigue. Now they've decided to take on one last job – showing a be...

#5
Oscar

Oscar

1991★ 6.3

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

Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making...

#6
Let's Make Love

Let's Make Love

1960★ 6.4

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

When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful...

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