Raab was a writer for GQ Magazine from 1992 until 1997, and was a regular contributor to Esquire from 1997 until 2016.[4] Much of his work at Esquire was one-on-one interviews with various celebrities (e.g. Phil Spector, Paul Giamatti, Don Zimmer).[5] The style of his non-interview writing is typically informal in nature, mainly in the voice of a storyteller.
Personal
Raab is a self-professed "fat Jew from Cleveland, a great deli town" who has mentioned on several occasions his anti-haute cuisine disposition.[5][6] Although not a food writer by trade, he has written frequently about the Cleveland food scene, and may be the biggest pundit of Slyman's Deli's award-winning corned-beef sandwich, which he has mentioned in more than one article appearing in Esquire.
He is a remarried divorcé, who currently lives in New Jersey with his wife and son.[7][8]
A fan of the Cleveland Indians, Raab has a tattoo of Chief Wahoo on his forearm, which he had done in a Dallas tattoo parlor during a 1994 interview with NBA player Dennis Rodman.[9][10][11] He has since advocated for the logo to be retired.[12]