Scott Raab was born in Cleveland, Ohio in 1952. The Raab family relocated to Los Angeles in 1960, but after his parents a divorced in 1962, he returned to Cleveland with his mother and two younger brothers. Raab graduated from Cleveland State in 1983 with a Bachelor's degree, and in 1986 received his Master's degree from the Iowa Writers' Workshop.

Raab was a writer for GQ Magazine from 1992 until 1997, and has been a regular contributor to Esquire from 1997 until the present. Much of his work at Esquire is one-on-one interviews with various celebrities (e.g. Phil Spector, Paul Giamati, Don Zimmer). The style of his non-interview writing is typically informal in nature, mainly in the voice of a storyteller variety.

Raab is a self-professed 'fat Jew from Cleveland, a great deli town' who has mentioned on several occasions his anti-haute cuisine disposition. 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. An avid fan of the Cleveland Indians, Raab has a tattoo of Chief Wahoo on his forearm, and a son.