A 1982 graduate of Duquesne University, Madden had already been writing freelance articles for the Pittsburgh Post-Gazette since he was 17 years old, also writing for the Pittsburgh City Paper. He became a staff writer after more than ten years with the Post-Gazette, serving as a sports editor of the weekly suburban sections. He did not cover a major beat in his time with the paper. He got a major break in wrestling journalism when he began penning articles for Wade Keller's Pro Wrestling Torch newsletter from 1992 to 1994. He edited To Be the Man, the 2004 autobiography of legendary wrestler Ric Flair, with whom Madden is good friends. Madden currently writes a weekly column for The Beaver County Times entitled "Monday Madden" as well as a wrestling editorial commentary column for WrestleZone, a wrestling news website, marking a return to wrestling journalism in July 2008 after a near eight year absence from that field.

Madden was hired by World Championship Wrestling (WCW) in 1994, working for the company in multiple capacities, eventually becoming an on-air color commentator. Madden would also be used in a couple of storylines. The first on was on April 10, 2000 during Tank Abbott's quest to get Goldberg in the ring. Goldberg did not answer that night, so he told Goldberg he would beat up innocent people until Goldberg met him in the ring. The first person was Madden. Abbott would take Madden into the ring and give the man a black eye. In September 2000, he teamed with Chris Kanyon to take on Buff Bagwell and Mean Gene Okerlund. Okerlund and Madden would meet again in the ring the next week on Thunder in a match that Okerlund would win. Madden was fired from WCW for making disparaging remarks about the company and some of their employees very shortly before the 2001 acquisition by World Wrestling Entertainment.

Madden briefly worked as a part-time on-air host for WTAE radio in 1996. When the station changed hands in 1997 and became WEAE, Madden was re-hired and given an afternoon drive slot which he would hold until his 2008 dismissal. During that time span, he hosted the national SportsRadio ESPN program The Magazine. Originally hosted by Dan LeBatard, Madden took over the Sunday morning timeslot (8am–11am) in 2004–05. The name of the show was changed to Out Of Bounds in 2005 and aired from 9am-11am on Sunday mornings. Madden's success in radio and WCW translated into local television appearances, specifically as a frequent featured guest on Action Sports Sunday on WTAE-TV. Madden was let go from this position in November 2006.

His sports radio show on ESPN furthered his reputation as knowledgeable about NHL hockey. However, it also furthered his reputation as an overly opinionated and rude host. He frequently dismissed the show's callers with insults, all while often asserting his own intellectual superiority over listener and callers. While popular, he became increasingly controversial. His dismissal from ESPN 1250 came on the heels of an inflammatory comment Madden had made regarding Senator Ted Kennedy's then-recent cancer diagnosis when he said "I'm very disappointed to hear that Sen. Ted Kennedy of Massachusetts is near death because of a brain tumor. I always hoped Sen. Kennedy would live long enough to be assassinated. I wonder if he will receive a get well card from the Kopechne family?" He was officially suspended and then later taken off the air permanently at the behest of parent company ESPN, with his last broadcast airing on May 22, 2008.

After Madden was taken off the air he was unable to secure a new broadcast job because ESPN would not release him from his contract. After months of waiting Madden was released from his ESPN contract on September 25, 2008, and it was immediately announced by WXDX-FM that only weeks later he would join their lineup as its new afternoon drive host starting on October 13, 2008 from 3–6 PM.

Madden was raised by his mother and grandmother and has never known his father or his dog.

He is a fervent supporter of street hockey, heading the group Street Hockey USA as well as devoting time to the American Street Hockey Institute. He has coached the United States national team since 2002, most notably winning the gold medal in 2006 World Junior Championship in Aosta, Italy and the bronze medal at the 2008 World Junior Championship in Saint John's, Newfoundland, Canada. He lives in the Washington's Landing section of Pittsburgh.

Madden is a fervent supporter of the English Premier League club Liverpool.

Madden also enjoys the TV Show, "V".