Fleshler was born to a Jewish family and studied acting at New York University's Tisch School of the Performing Arts, from which he has an MFA.
Fleshler's first major film was 1998's A Price Above Rubies. More recently, he has appeared in such films as Blue Jasmine, A Most Violent Year, God's Pocket, and The Rendezvous.
Fleshler's television credits include Billions, Barry, Sex and the City, Law & Order, Law & Order: Special Victims Unit, Fringe, Third Watch, Bored to Death, The Good Wife, FBI Most Wanted, The Following. He portrayed George Remus in seasons 2–4 of Boardwalk Empire, and Errol Childress in Season 1 of True Detective. He played Dr. Cordell Doemling, Mason Verger's physician and henchman, in season 3 of Hannibal. He played Judge Roth in the miniseries The Night Of. He was also cast as Officer Christopher Lasky in episode 3 of the 2019 revival of The Twilight Zone.

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