Dynamic Watchlist Hub: May 10, 2026

10 Best Movies Like Michael and Madonna 2

If you loved Michael and Madonna 2, 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 Michael and Madonna 2.

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#1
Held Up

Held Up

1999★ 5.8

Why watch this? A perfect follow-up to Michael and Madonna 2 for fans of Comedy. It captures a similar light-hearted atmosphere.

What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is...

#2
Chris Rock: Kill the Messenger

Chris Rock: Kill the Messenger

2008★ 7.6

Why watch this? A perfect follow-up to Michael and Madonna 2 for fans of Comedy. It captures a similar light-hearted atmosphere.

An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket)...

#3
The Wedding Year

The Wedding Year

2019★ 6.0

Why watch this? A perfect follow-up to Michael and Madonna 2 for fans of Comedy. It captures a similar light-hearted atmosphere.

A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year....

#4
The Hangover Part III

The Hangover Part III

2013★ 6.2

Why watch this? A perfect follow-up to Michael and Madonna 2 for fans of Comedy. It captures a similar light-hearted atmosphere.

This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off....

#5
Pitch Perfect 3

Pitch Perfect 3

2017★ 6.5

Why watch this? A perfect follow-up to Michael and Madonna 2 for fans of Comedy. It captures a similar light-hearted atmosphere.

After the highs of winning the world championships, the Bellas find themselves split apart and discovering there aren't job prospects for making music with your mouth. But when the...

#6
YES DAY

YES DAY

2021★ 6.7

Why watch this? A perfect follow-up to Michael and Madonna 2 for fans of Comedy. It captures a similar light-hearted atmosphere.

A mom and dad who usually say no decide to say yes to their kids' wildest requests — with a few ground rules — on a whirlwind day of fun and adventure....

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