Win It All poster
Where to stream

Win It All

5.720171h 28mMovieComedy

A gambling addict faces a conflict when entrusted with keeping a bunch of money that isn't his.

DirectorJoe Swanberg
WritersJoe Swanberg·Jake Johnson
ProducersJake Johnson·Joe Swanberg

Where to watch

Not available in Canada
Streaming in 1 other country

Win It All isn't on any streaming service in Canada right now, but it's available in Germany. Streaming rights are licensed per country.

Cast · Directed by Joe Swanberg

JJJake Johnson
Jake Johnson
Eddie Garrett
ADAislinn Derbez
Aislinn Derbez
Eva
JTJoe Lo Truglio
Joe Lo Truglio
Ron
KKKeegan-Michael Key
Keegan-Michael Key
Gene
NE
Nicky Excitement
Nick
RS
Rony Shemon
Rony
MN
Morgan Ng
Chinatown Casino Doorman
EK
Edward Kaihatsu
Chinatown Casino Bartender
AJ
Adrian Jasso
Adrian
JGJosé Antonio García
José Antonio García
Michael
JSJude Swanberg
Jude Swanberg
Jude
KRKris Rey
Kris Rey
Kris

More from Jake Johnson · Lead actor

Curb Your Enthusiasm
Curb Your Enthusiasm
2000 · 8.1
New Girl
New Girl
2011 · 7.4
BoJack Horseman
BoJack Horseman
2014 · 8.5
We Bare Bears
We Bare Bears
2015 · 7.7
Lie to Me
Lie to Me
2009 · 7.9
The Unit
The Unit
2006 · 7.4
Spider-Man: Across the Spider-Verse
Spider-Man: Across the Spider-Verse
2023 · 8.4
Spider-Man: Into the Spider-Verse
Spider-Man: Into the Spider-Verse
2018 · 8.4
Mythic Quest
Mythic Quest
2020 · 7.2
The Mummy
The Mummy
2017 · 5.5
See all fromJake Johnson

More from Aislinn Derbez · Co-star actress

Until the End of the World
Until the End of the World
2026 · 7.9
Easy
Easy
2016 · 6.0
The House of Flowers
The House of Flowers
2018 · 7.7
Killer Women
Killer Women
2008 · 7.6
Back to the Outback
Back to the Outback
2021 · 7.6
Seis Manos
Seis Manos
2019 · 6.6
Between Walls
Between Walls
2025 · 6.9
Miss Bala
Miss Bala
2019 · 6.3
The House of Flowers Presents: The Funeral
The House of Flowers Presents: The Funeral
2019 · 7.0
Broken Promises
Broken Promises
2013 · 7.3
See all fromAislinn Derbez

More from Joe Swanberg · Director

Looking
Looking
2014 · 7.5
Easy
Easy
2016 · 6.0
V/H/S
V/H/S
2012 · 6.1
Drinking Buddies
Drinking Buddies
2013 · 6.0
The Sun Never Sets
The Sun Never Sets
2026 · 9.5
Happy Christmas
Happy Christmas
2014 · 5.1
Digging for Fire
Digging for Fire
2015 · 5.2
Autoerotic
Autoerotic
2011 · 4.1
Alexander the Last
Alexander the Last
2009 · 4.6
All the Light in the Sky
All the Light in the Sky
2013 · 5.0
See all fromJoe Swanberg

More like this

Greedy
Greedy
1994 · 6.2
The Three Stooges
The Three Stooges
2012 · 5.8
Horrible Bosses 2
Horrible Bosses 2
2014 · 6.2
Buddy Buddy
Buddy Buddy
1981 · 6.1
Happy Gilmore
Happy Gilmore
1996 · 6.7
The Comeback Trail
The Comeback Trail
2020 · 5.8
Stark Raving Mad
Stark Raving Mad
2002 · 6.1
Oscar
Oscar
1991 · 6.4
Hot Rod
Hot Rod
2007 · 6.4
Grandma's Boy
Grandma's Boy
2006 · 6.5
Thunderstruck
Thunderstruck
2012 · 6.2
Taking Care of Business
Taking Care of Business
1990 · 6.3

Win It All — streaming FAQ

Which OTT platform streams Win It All?

Win It All isn't on any streaming service in Canada yet, but it's available in Germany. Streaming rights differ by country — switch your country in the header to see where.

Is Win It All on Netflix?

No, Win It All is not on Netflix in Canada as of October 2026.

Is Win It All on Amazon Prime Video?

No, Win It All isn't on Amazon Prime Video in Canada right now.

Where can I watch Win It All for free?

Win It All isn't streaming in Canada yet, so there's no way to watch it free at the moment.