Two If by Sea poster
Where to stream

Two If by Sea

5.019961h 36mRMovieComedyRomance

Frank O'Brien, a petty thief, and his 7-year-long girlfriend Roz want to put an end to their unsteady lifestyle and just do that last job, which involves stealing a valuable painting. Frank takes Roz to an island on the coast of New…

DirectorBill Bennett
WritersDenis Leary·Mike Armstrong
ProducersGary Barber·James G. Robinson

Where to watch

NetflixNetflixNetflix Standard with AdsNetflix Standard with Ads
Availability shown for Canada · rights vary by country

Cast · Directed by Bill Bennett

SBSandra Bullock
Sandra Bullock
Roz
DLDenis Leary
Denis Leary
Francis 'Frank' O'Brien
YKYaphet Kotto
Yaphet Kotto
FBI Agent O'Malley
SDStephen Dillane
Stephen Dillane
Evan Marsh
TJTracey Cherelle Jones
Tracey Cherelle Jones
Cop
JBJulia Montgomery Brown
Julia Montgomery Brown
Beautiful Woman
JMJane Moffat
Jane Moffat
Marcy Kellerher
MSMike Starr
Mike Starr
Fitzie
JTJonathan Tucker
Jonathan Tucker
Todd
WRWayne Robson
Wayne Robson
Beano Callahan
MBMichael Badalucco
Michael Badalucco
Quinn
AMAngela Moore
Angela Moore
Nanny

More from Sandra Bullock · Lead actress

Practical Magic 2
Practical Magic 2
2026 · 7.2
Premonition
Premonition
2007 · 6.3
Bullet Train
Bullet Train
2022 · 7.4
The Proposal
The Proposal
2009 · 7.2
Practical Magic
Practical Magic
1998 · 6.8
HBO First Look
HBO First Look
1992 · 5.5
Gravity
Gravity
2013 · 7.2
Speed
Speed
1994 · 7.2
Ocean's Eight
Ocean's Eight
2018 · 6.9
The Prince of Egypt
The Prince of Egypt
1998 · 7.3
See all fromSandra Bullock

More from Denis Leary · Co-star actor

The Simpsons
The Simpsons
1989 · 8.0
Family Guy
Family Guy
1999 · 7.4
Animal Kingdom
Animal Kingdom
2016 · 7.8
Law & Order: Organized Crime
Law & Order: Organized Crime
2021 · 7.9
Rescue Me
Rescue Me
2004 · 7.6
Spider-Man: Across the Spider-Verse
Spider-Man: Across the Spider-Verse
2023 · 8.3
The Amazing Spider-Man
The Amazing Spider-Man
2012 · 6.8
Ice Age
Ice Age
2002 · 7.4
Dr. Katz, Professional Therapist
Dr. Katz, Professional Therapist
1995 · 7.8
The Amazing Spider-Man 2
The Amazing Spider-Man 2
2014 · 6.6
See all fromDenis Leary

More from Bill Bennett · Director

Bollywood Hero
Bollywood Hero
2009 · 6.3
Tempted
Tempted
2001 · 4.8
The Nugget
The Nugget
2002 · 5.8
Spider and Rose
Spider and Rose
1994 · 6.3
In a Savage Land
In a Savage Land
1999 · 4.8
A Street to Die
A Street to Die
1985 · 6.8
Kiss or Kill
Kiss or Kill
1997 · 4.5
Uninhabited
Uninhabited
2010 · 4.5
The Way, My Way
The Way, My Way
2024 · 6.5
PGS: Personal Guidance System
PGS: Personal Guidance System
2017
See all fromBill Bennett

More like this

Confess, Fletch
Confess, Fletch
2022 · 6.2
Out of Sight
Out of Sight
1998 · 6.7
Ordinary Decent Criminal
Ordinary Decent Criminal
2000 · 6.2
The Instigators
The Instigators
2024 · 6.1
Greedy People
Greedy People
2024 · 6.3
No Hard Feelings
No Hard Feelings
2023 · 6.7
Palookaville
Palookaville
1996 · 5.9
The Pickup
The Pickup
2025 · 6.4
Thunderbolt and Lightfoot
Thunderbolt and Lightfoot
1974 · 6.8
The Heat
The Heat
2013 · 6.6
Quick Change
Quick Change
1990 · 6.7
Starting Over
Starting Over
1979 · 6.4

Two If by Sea — streaming FAQ

Which OTT platform streams Two If by Sea?

Two If by Sea is streaming on Netflix and Netflix Standard in Canada.

Is Two If by Sea on Netflix?

Yes — Two If by Sea is available on Netflix in Canada as of November 2026.

Is Two If by Sea on Amazon Prime Video?

No, Two If by Sea isn't on Amazon Prime Video in Canada right now. It's on Netflix and Netflix Standard instead.

Where can I watch Two If by Sea for free?

Two If by Sea is available on Netflix and Netflix Standard in Canada, but you'll need an active subscription — there's no free option right now.