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Movies Like Can't Win. Do Try. (What to Watch After)

Fans of Can't Win. Do Try., are likely to find resonance in stories that questions the purpose and weight of our choices while delivering targets the intellect with complex, multi-layered ideas. Carefully balances character depth with narrative flow makes this a perfect follow-up for your next session.

Mood Breakdown
Runtime Cluster

Standard feature-length experiences.

Viewer Fit

Best for fans of who appreciate concise storytelling.

Top Picks

Landline
6.1

Landline

2017

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

Almost Friends
6.3

Almost Friends

2017

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 serious boyfriend. As they become closer, the line between friendship and intimacy is blurred, and the situation forces both to examine where they are in their lives.

The Lords of Flatbush
5.8

The Lords of Flatbush

1974

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 street fights, and hang out at a local malt shop.

Heights
6.3

Heights

2005

Spanning twenty-four hours, HEIGHTS follows five New Yorkers challenged to choose their destiny before the sun comes up the next day.

XX/XY
5.8

XX/XY

2002

Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.

Drive Me Crazy
6.5

Drive Me Crazy

1999

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 romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought.

Newness
6.0

Newness

2017

In contemporary Los Angeles, two millennials navigating a social media–driven hookup culture begin a relationship that pushes both emotional and physical boundaries.

Carnal Knowledge
6.6

Carnal Knowledge

1971

Two lifelong friends navigate complex sexual encounters and emotional entanglements, wrestling with societal norms and personal desires.

More Movies Like Can't Win. Do Try.

As Cool as I Am
5.8

As Cool as I Am

2013

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

The Wackness
6.4

The Wackness

2008

Set in New York City in the sweltering summer, The Wackness tells the story of a troubled teenage drug dealer, who trades pot for therapy sessions with a drug-addled psychiatrist. Things get more complicated when he falls for one of his classmates, who just happens to be the doctor's daughter. This is a coming-of-age story about sex, drugs, music and what it takes to be a man.

Juniper
6.5

Juniper

2021

When a self-destructive teenager is suspended from school and asked to look after his feisty alcoholic grandmother as a punishment, the crazy time they spend together turns his life around.

(Untitled)
6.4

(Untitled)

2009

A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art.

SubUrbia
6.2

SubUrbia

1997

A group of suburban teenagers try to support each other through the difficult task of becoming adults.

Daddy Longlegs
6.6

Daddy Longlegs

2010

After months of living a solitary existence, Lenny, 34, picks up his kids from school. Every year he spends a couple of weeks with his sons Sage, 9, and Frey, 7. Lenny hosts his kids within a midtown studio apartment in New York. During these two weeks, he must figure out if he wants to act as their father or be their friend. Ultimately, their trip upstate results in complete lawlessness taking over their lives.

Anniversary
6.8

Anniversary

2025

When Ellen and Paul’s son Josh introduces his new girlfriend at their 25th anniversary party, no one suspects that it is the beginning of the end for this happy family. The new girlfriend is Liz, Ellen’s former student, who left the university, some years before, after Ellen called her out in class for her radical ideology.

Real Women Have Curves
6.1

Real Women Have Curves

2002

In East Los Angeles, an 18-year-old struggles between her ambitions of going to college and the desires of her domineering mother for her to get married, have children, and oversee the small, rundown family-owned textile factory.

Winter Spring Summer or Fall
7.2

Winter Spring Summer or Fall

2024

Remi and Barnes, two very different teenagers, meet by chance in the winter of their senior year, then spend four days together over the course of a year that will change their lives forever.

Match
5.9

Match

2014

A Seattle couple travel to New York to interview colorful former dancer Tobi for research on a dissertation about dance. But soon, common niceties and social graces erode when the questions turn personal and the true nature of the interview is called into question.

What's Love Got to Do with It?
6.0

What's Love Got to Do with It?

2023

Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.

On the Edge
6.6

On the Edge

2001

A suicidal young man is committed to a Dublin psychiatric hospital where he meets new friends who greatly influence his life.

Why These Movies Are Similar

These recommendations share core qualities with Can't Win. Do Try. (2016): Drama and Comedy themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Can't Win. Do Try..

See full details for Can't Win. Do Try. (2016)

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