History of Dean Winters in Timeline

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Dean Winters

Dean Winters is a prolific American actor, widely recognized for his portrayal of complex characters across diverse television series and films. His notable roles include Ryan O'Reily in the HBO drama "Oz," and appearances in "Millennium," "Rescue Me," "30 Rock," "Sex and the City," and "Law & Order: Special Victims Unit." Beyond these, Winters gained significant popularity as "Mayhem" in Allstate Insurance commercials. He also featured in "Battle Creek," "Brooklyn Nine-Nine," the Netflix film "The Out-Laws," and "Monsieur Spade." His career is marked by a consistent presence in both dramatic and comedic roles, showcasing his versatility as an actor.

July 20, 1964: Birth of Dean Winters

Dean Winters was born on July 20, 1964.

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July 30, 1964: Birth of Dean Winters

Dean Winters was born on July 30, 1964 in New York City.

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1982: Graduation from Brophy College Preparatory

Dean Winters graduated from Brophy College Preparatory in 1982.

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1986: Graduation from Colorado College

Dean Winters graduated from Colorado College in 1986.

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1999: Role in "Undercover Angel"

In 1999, Dean Winters starred in the romantic comedy "Undercover Angel" with Yasmine Bleeth.

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2002: Role in "Hellraiser: Hellseeker"

Dean Winters starred in the direct-to-video horror film "Hellraiser: Hellseeker" in 2002.

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2009: Health Issues and Amputations

In 2009, Dean Winters suffered a bacterial infection, cardiac arrest, and subsequent gangrene, leading to the amputation of two toes and part of a thumb.

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2010: Return to Acting and "Mayhem" Role

Dean Winters returned to acting in 2010 with a role on "30 Rock", and also began portraying "Mayhem" in Allstate Insurance commercials.

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May 2015: Cancellation of "Battle Creek"

The CBS cop drama series "Battle Creek", in which Dean Winters co-starred, was canceled in May 2015.

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2018: Role as Mr. Town in "American Gods"

Dean Winters was cast as Mr. Town in the second season of "American Gods" in 2018.

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2019: Role in "Framing John DeLorean"

Dean Winters appeared in the film "Framing John DeLorean" in 2019.

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2019: Collaboration with Tina Fey on "Mayhem" Commercials

In 2019, Tina Fey joined Dean Winters in a series of "Mayhem" commercials for Allstate.

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2023: Appearance in "The Out-Laws"

Dean Winters appeared in the Netflix film "The Out-Laws" in 2023.

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2024: Role in "Monsieur Spade"

Dean Winters appeared in the AMC series "Monsieur Spade" in 2024.

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