Dean Winters

Dean Winters

Dean Winters (born July 20, 1964) is an American actor, who is known for his roles as Bobby on the YouTube series Wayne, Detective Brian Cassidy on Law & Order: SVU, Detective Russ Agnew on Battle Creek, ‘The Vulture’ Detective Pembroke on Brooklyn Nine-Nine, Charley Dixon on FOX’s Terminator: The Sarah Connor Chronicles, Dennis Duffy on NBC’s 30 Rock, Johnny Gavin on FX’s Rescue Me, Ryan O’Reily on HBO’s Oz. He also portrays “Mayhem” in Allstate commercials.

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Dean Winters Movies

Discover the best Dean Winters movies. Explore the complete filmography, including top-rated classics, newest releases, and highest-grossing films starring Dean Winters ranked by year and score.

1
Highest 2 Lowest

Highest 2 Lowest (2025)

Crime Drama Thriller
He built an empire by hearing what others missed, a music mogul whose instincts turned artists into legends. But when a ransom plot lands on his doorstep, all that power...
Score 5.5
2
Rough Night

Rough Night (2017)

Comedy Drama
A decade after college, five women descend on Miami for one last blowout before the bride-to-be trades in her freedom for a wedding ring. The weekend unravels spectacularly when a...
Score 5.7
3
John Wick

John Wick (2014)

Action Thriller
Retirement suited John Wick well enough, until it didn't. He had buried his wife, accepted her parting gift of a beagle puppy, and made his peace with a quieter life....
Score 7.4
4
Conspiracy Theory

Conspiracy Theory (1997)

Action Drama Mystery
Jerry Fletcher is a New York cabdriver who sees plots everywhere, filling newsletters with theories about mind control, shadowy governments, and hidden agendas. Most people dismiss him as harmless. Then...
Score 6.6

Dean Winters TV Shows

Browse the ultimate list of Dean Winters TV shows. Find top-rated television series, critically acclaimed dramas, and hit shows starring Dean Winters.

1
Oz

Oz (1997)

Crime Drama
Inside Oswald Maximum Security Prison, a progressive pod called Emerald City was supposed to represent a better way. Instead, it became a pressure cooker where rival factions, Aryan supremacists, Italian...
Score 8.0

Frequently Asked Questions

What are the highest-rated movies starring Dean Winters? +
According to aggregate user scores, the absolute best titles starring Dean Winters are Highest 2 Lowest, Rough Night, and John Wick.
How many movies and TV shows has Dean Winters starred in? +
Our database currently features a comprehensive filmography of 5 titles starring Dean Winters, ranging from their earliest roles to the newest releases.
Are the movies starring Dean Winters worth watching? +
Yes! The overall filmography starring Dean Winters maintains a strong average user rating of 6.6 out of 10 across all tracked titles.