Dynamic Watchlist Hub: Apr 14, 2026

10 Best Movies Like Can't Win. Do Try.

If you loved Can't Win. Do Try., 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 Can't Win. Do Try..

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#1
ATL

ATL

2006★ 6.9

Why watch this? A perfect follow-up to Can't Win. Do Try. for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

As four friends prepare for life after high school, different challenges bring about turning points in each of their lives. The dramas unfold and resolve at their local rollerskati...

#2
Landline

Landline

2017★ 6.1

Why watch this? A perfect follow-up to Can't Win. Do Try. for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair....

#3
Almost Friends

Almost Friends

2017★ 6.3

Why watch this? A perfect follow-up to Can't Win. Do Try. for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

A man in his mid-20s, still living at home with his mother and stepfather, puts all his eggs in one basket: the girl who works at his local coffee shop. The problem is, she has a s...

#4
As Cool as I Am

As Cool as I Am

2013★ 5.8

Why watch this? A perfect follow-up to Can't Win. Do Try. for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

A smart teenage girl comes of age in a small town with her self-centered parents who had her when they were teenagers....

#5
Drive Me Crazy

Drive Me Crazy

1999★ 6.6

Why watch this? A perfect follow-up to Can't Win. Do Try. for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective...

#6
The Lords of Flatbush

The Lords of Flatbush

1974★ 5.8

Why watch this? A perfect follow-up to Can't Win. Do Try. for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

Set in 1958, the coming of age story follows four lower middle-class Brooklyn teenagers known as The Lords of Flatbush. The Lords chase girls, steal cars, shoot pool, get into stre...

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