Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Lucky Loser

If you loved Lucky Loser, 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 Lucky Loser.

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#1
Men in the City

Men in the City

2009★ 6.2

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

Follows six very different men and their struggles with women, family and work. Yet, they are somehow connected to each other....

#2
Taking Care of Business

Taking Care of Business

1990★ 6.3

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

An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him....

#3
Jim Jefferies: Freedumb

Jim Jefferies: Freedumb

2016★ 7.3

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

Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee....

#4
Mr. Bones

Mr. Bones

2001★ 6.0

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

A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament....

#5
The Ladies Man

The Ladies Man

1961★ 6.3

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

After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women...

#6
Adventures in Public School

Adventures in Public School

2018★ 6.3

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

A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes....

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