Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Middle Man

If you loved Middle Man, 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 Middle Man.

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#1
Very Bad Things

Very Bad Things

1998★ 6.3

Why watch this? A perfect follow-up to Middle Man for fans of Comedy & Crime & Thriller. It captures a similar light-hearted atmosphere.

Kyle Fisher has one last night to celebrate life as a single man before marrying Laura, so he sets out to Vegas with four of his best buddies. But a drug and alcohol filled night o...

#2
Fun with Dick and Jane

Fun with Dick and Jane

1977★ 6.6

Why watch this? A perfect follow-up to Middle Man for fans of Comedy & Crime. 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
Dave Chappelle: The Unstoppable...

Dave Chappelle: The Unstoppable...

2025★ 6.6

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

Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special....

#4
Chris Rock: Bigger & Blacker

Chris Rock: Bigger & Blacker

1999★ 7.4

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

Chris Rock brings his critically acclaimed brand of social commentary-themed humour to this HBO Special, extolling his razor-sharp wit and wisdom on such topics as gun control, Pre...

#5
Panic

Panic

2000★ 6.2

Why watch this? A perfect follow-up to Middle Man for fans of Drama & Crime. It captures a similar emotionally gripping atmosphere.

Alex is going through a midlife crisis and it has become a very difficult time for him. His marriage is struggling, he's worried about his son, and his job of killing people for hi...

#6
68 Kill

68 Kill

2017★ 5.9

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

Chip's problem is that he can't say no to beautiful women. This weakness gets him into a world of trouble when he agrees to help his girlfriend steal $68,000....

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