Pearlman is the author of The Bad Guys Won a biography of the 1986 New York Mets with the subtitle, "A Season of Brawling, Boozing, Bimbo-chasing and Championship Baseball with Straw, Doc, Mookie, Nails, The Kid, and the Rest of the 1986 Mets, the Rowdiest Team Ever to Put on a New York Uniform--and Maybe the Best." In 2004, the book spent eight weeks on the New York Times Best Seller list. Pearlman followed that up with his 2006 publication of Love Me, Hate Me an unauthorized biography of Barry Bonds for which the author said he interviewed 524 subjects. Pearlman said that because Love Me, Hate Me was released three weeks after Game of Shadows, it quickly faded. His third book, Boys Will Be Boys, on the 1990s Dallas Cowboys dynasty, spent 10 weeks on the New York Times best-seller's list. His fourth book, a biography of Roger Clemens titled, "The Rocket That Fell to Earth," was released by HarperCollins on March 24, 2009. The book is a detailed account of Clemens' life on and off the baseball field.

Pearlman was born and raised in Mahopac, New York. He got his start in journalism in 1989, when he interned at a weekly newspaper in Cross River, entitled "The Patent Trader". After graduating from the University of Delaware, he was hired as a food and fashion writer by The Tennessean in Nashville. In 1996, Pearlman was hired by Sports Illustrated, where he spent nearly seven years as a baseball writer.

In 2002, Pearlman left Sports Illustrated and spent the next two years at Newsday, but left to focus on writing books. He also keeps an unusually personal online blog, where he has written about such intimate issues as seeing a rival book get publicity in Sports Illustrated, where he worked,, or finding blood in his feces after using the toilet..

He was a frequent contributor to ESPN.com's Page 2, then as a columnist for SI.com. In the fall of 2007, Pearlman wrote several controversial articles on Page 2 regarding the lack of a rivalry between the University of Delaware's and Delaware State University's football teams. The article brought national attention to this disparity. The University of Delaware and Delaware State finally played a football game on November 23, 2007 at part of the NCAA FCS playoffs. University of Delaware won the game with a score of 44-7.