Dynamic Watchlist Hub: Apr 10, 2026

10 Best Movies Like Sidewalks of New York

If you loved Sidewalks of New York, 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 Sidewalks of New York.

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#1
The Giant Mechanical Man

The Giant Mechanical Man

2012★ 6.5

Why watch this? A perfect follow-up to Sidewalks of New York for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him....

#2
Numb

Numb

2007★ 5.9

Why watch this? A perfect follow-up to Sidewalks of New York for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink,...

#3
Jack Goes Boating

Jack Goes Boating

2010★ 6.0

Why watch this? A perfect follow-up to Sidewalks of New York for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples....

#4
Irreplaceable You

Irreplaceable You

2018★ 6.9

Why watch this? A perfect follow-up to Sidewalks of New York for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating....

#5
The Best You Can

The Best You Can

2025★ 7.0

Why watch this? A perfect follow-up to Sidewalks of New York for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, ...

#6
Enemies, a Love Story

Enemies, a Love Story

1989★ 6.2

Why watch this? A perfect follow-up to Sidewalks of New York for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife....

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