Perhaps you've seen Dean Winters as Tommy Gavin's angry brother on Rescue Me, or as Liz Lemon's dummy boyfriend Dennis Duffy on 30 Rock. My first introduction to him was in the HBO series Oz as the terrifying O'Reilly. Now, he can be seen all the time as Mayhem in the ubiquitous AllState Insurance ads. But come Thursday, you'll find him on NBC's Up All Night, where he'll portray Will Arnett's older brother.
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