Wilbon began working for The Washington Post in 1980 after summer internships at the newspaper in 1979 and 1980. He covered college sports, Major League Baseball, the National Football League and the National Basketball Association before being promoted to full-time columnist in February 1990. His column in the Post, which deals as much with the culture of sports as the action on the court or field, appears up to four times a week.

In his career, Wilbon has covered ten Summer and Winter Olympic Games for The Washington Post, every Super Bowl since 1987, nearly every Final Four since 1982 and each year's NBA Finals since 1987.

After contributing to ESPN's The Sports Reporters and other shows on the cable network, he began co-hosting ESPN's daily Pardon the Interruption (PTI) with Tony Kornheiser on October 22, 2001. He is also a member of ABC's NBA Countdown (with host Stuart Scott and analyst Jon Barry) which is the pre-game show for the network's NBA telecasts.

In addition to his work at The Washington Post, PTI and ESPN, Wilbon appeared weekly on WRC-TV in Washington, D.C. with WRC Sports Director George Michael, and Pro Football Hall of Famers John Riggins and Sonny Jurgensen on Redskins Report during the football season. He also appeared with Michael, USA Today basketball writer David DuPree and Tony Kornheiser on Full Court Press during the basketball season. Both of these shows were canceled in December 2008 due to budget cuts. In 2001 Wilbon was named the top sports columnist by the Society of Professional Journalists.Wilbon also forged a close friendship with former Marshall and current NFL quarterback Byron Leftwich while the young passer was a standout player for HD Woodson in Washington, D.C.In recent years, he has become more known as an ESPN personality, and in late 2006, agreed to a multi-year contract extension with ESPN that will give the network priority in conflicts with his newspaper assignments. The first major example of this happened on February 4, 2007, when Wilbon covered a Detroit Pistons-Cleveland Cavaliers game instead of Super Bowl XLI.

Born in the south side of Chicago, Illinois, Wilbon graduated from St. Ignatius College Preparatory School in 1976 and received his journalism degree in 1980 from Northwestern University's Medill School of Journalism. Wilbon currently lives in Bethesda, Maryland, but he also has a home in Scottsdale, Arizona.

Wilbon was a pitcher in high school and once threw a one hitter.

As a native of Chicago, Wilbon generally favors Chicago area teams including the Chicago Bulls, Chicago Bears, Chicago Blackhawks and the north-side Chicago Cubs.

Wilbon is good friends with former NBA star Charles Barkley and has edited and written the introduction for his most recent books, "I May Be Wrong But I Doubt It" and "Who's Afraid of a Large Black Man?", both of which were New York Times best sellers.

Wilbon has a cousin, Travon Bellamy, who plays for the University of Illinois football team.

Wilbon suffered a mild heart attack on January 27, 2008. After complaining of chest pains, he was taken to a Scottsdale hospital where doctors performed an angioplasty. Sports Media Watch: ESPN's Wilbon has heart attack

Wilbon is a known diabetic.

Wilbon and his wife Sheryl Wilbon had their first child, Matthew Raymond Wilbon, via surrogate on March 26, 2008. Matthew is often referred to as "Lilbon" by the aforementioned Tony Kornheiser on his radio show.

On August 10, 2008, during a Cubs-Cardinals game at Wrigley Field, Wilbon threw out the ceremonial first pitch and then sang "Take Me Out to the Ballgame" as part of the seventh-inning stretch. Footage of Wilbon wearing a tucked-in Cubs jersey and bouncing the pitch is frequently shown on Pardon The Interruption as a friendly teasing by Kornheiser.

In May 2009, Wilbon competed in a made-for-TV "King of Bowling" show against pro bowling star Wes Malott. Wilbon beat Malott by a score of 256-248, but Wilbon received a 57-pin handicap and Malott had to use a plastic ball.