Dynamic Watchlist Hub: Feb 03, 2026

10 Best Movies Like The First $20 Million Is Always the Hardest

If you loved The First $20 Million Is Always the Hardest, 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 First $20 Million Is Always the Hardest.

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#1
Hostage

Hostage

2005★ 6.3

Why watch this? A perfect follow-up to The First $20 Million Is Always the Hardest for fans of Action. It captures a similar adrenaline-pumping atmosphere.

When a mafia accountant is taken hostage on his beat, a police officer – wracked by guilt from a prior stint as a negotiator – must negotiate the standoff, even as his own family i...

#2
Head Over Heels

Head Over Heels

2001★ 5.6

Why watch this? A perfect follow-up to The First $20 Million Is Always the Hardest for fans of Comedy. It captures a similar light-hearted atmosphere.

Ordinary single girl Amanda Pierce unexpectedly finds herself sharing an awesome Manhattan apartment with four sexy supermodels. Determined to bring Amanda into their world, the mo...

#3
The Gingerbread Man

The Gingerbread Man

1998★ 5.6

Why watch this? A perfect follow-up to The First $20 Million Is Always the Hardest for fans of Thriller. It captures a similar compelling atmosphere.

A successful Savannah defense attorney gets romantically involved with a sexy, mysterious waitress troubled by psychopaths and dark family secrets....

#4
Honey

Honey

2003★ 6.3

Why watch this? A perfect follow-up to The First $20 Million Is Always the Hardest for fans of Music. It captures a similar emotionally gripping atmosphere.

Honey Daniels dreams of making a name for herself as a hip-hop choreographer. When she's not busy hitting downtown clubs with her friends, she teaches dance classes at a nearby com...

#5
The Switch

The Switch

2010★ 6.2

Why watch this? A perfect follow-up to The First $20 Million Is Always the Hardest for fans of Comedy. It captures a similar light-hearted atmosphere.

Kassie is a smart, fun-loving single woman who, despite her neurotic best friend Wally’s objections, decides it’s time to have a baby – even if it means doing it herself… with a li...

#6
Anchorman 2: The Legend Continues

Anchorman 2: The Legend Continues

2013★ 6.1

Why watch this? A perfect follow-up to The First $20 Million Is Always the Hardest for fans of Comedy. It captures a similar light-hearted atmosphere.

With the 70s behind him, San Diego's top rated newsman, Ron Burgundy, returns to take New York's first 24-hour news channel by storm....