- Died in the back of an ambulance going through Central Park in 2009 after suffering from a bacterial infection. He was brought back to life 3-1/2 minutes later by the emergency response team at Lenox Hill Hospital. In a span of two years he had 16 surgeries, lost 2-1/2 toes and half a thumb after contracting gangrene. He also had major reconstructive surgery on his left arm. He was offered the role of "Mayhem" for Allstate's ad campaign while in the hospital.
- Did a summer intensive at the Royal Academy of Dramatic Art (RADA) in London, England. His acting partner was Rashida Jones.
- While working at a bar with his brother Scott William Winters, Dean met Tom Fontana, who wrote him a part on the TV series Homicide: Life on the Street (1993) for his 30th birthday.
- Credits Tina Fey with bringing his career back to life on "30 Rock" (2006).
- The role of "Ryan O'Reily" on Oz (1997) (HBO) was written and created by Tom Fontana for Dean. Part of Fontana's master plan was to bring Scott William Winters (Dean's brother) on "Oz" for Season 2. Brad Winters, Dean's other brother, also worked on "Oz" as a writer. Blair Winters, Dean's sister, married "Oz" producer/writer Jorge Zamacona.
- He studied art history in London (England) and Florence (Italy), where he studied Italian.
- Credits Rita Moreno as his favorite acting mentor/best friend.
- He was one of the founding actors in the Workhouse Theater in Tribeca.
- He started out on the bartending circuit working in bars and clubs around Manhattan.
- Of Irish and Italian descent, Dean Winters was raised in Long Island along with his younger brothers and sister ( Scott William Winters, Blair Winters, and Bradford Winters), the children of Patrick (an electronics engineer) and Magna Winters.
- He said that two moments defined his path: his brother Scott William Winters dragging him down to meet famed acting coach William Esper (with whom Dean studied) and watching Sean Penn's The Indian Runner (1991).
- As an actor, he was highly influenced by Rita Moreno.
- Attended Hommocks Middle School, which turned out Matt Dillon and Kevin Dillon, as well as Dean's brother, Scott William Winters. At age 14, Dean moved to Scottsdale, Arizona, where his grandparents lived and attended Chaparral High School. He later graduated from Brophy College Preparatory, a Jesuit school in Phoenix, before going on to attend Colorado College.
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