Doleman played football collegiately at the University of Pittsburgh. He was a star linebacker and defensive end for the Pitt Panthers from 1981 to 1984. He ended his career at Pitt with 25 sacks which was good for third all-time at the time of his departure. That total still ranks sixth in Pitt annals.
Doleman was selected by the Minnesota Vikings in the 1st round (4th overall) of the 1985 NFL Draft. He began his NFL career as an outside linebacker in the Vikings 3-4 defense. However, the team switched to a 4-3 defense early in his career. The move paid off for Doleman, who recorded 21 sacks in the 1989 season, the highest total recorded that season and the fourth highest total ever. The 21 sacks in a single season was a Vikings record until Jared Allen recorded 22 sacks in 2011. Doleman later played for the Atlanta Falcons and the San Francisco 49ers before returning to the Vikings in 1999 for his final season.
In 2010 Doleman founded the Celebrity Charitable Network, a consulting firm that works with athletes, musicians and other media personalities to support their philanthropic fundraising efforts. The Celebrity Charitable Network is based in Atlanta and serves clientele throughout the country in all genres of entertainment.
In February of 2012 Doleman was elected to the Pro Football Hall of Fame . Although he played for three different franchises in his storied career, he chose to go into the Hall of Fame as a Minnesota Viking, where his playing days began as a first round pick in 1985 and ended as a respected veteran in 1999. On August 4, 2012 Doleman was officially inducted into the Pro Football Hall of Fame at the Enshrinement Ceremony in Canton, Ohio. Doleman's son Evan introduced him before his bust, sculpted by Scott Myers, was unveiled.
In October of 2013 Doleman participated in the Golf Channel reality series Big Break NFL Puerto Rico. The competition took place at the Dorado Beach Resort with a premise that featured former NFL greats partnered with 2 aspiring professional golfers. Each episode the teams were given multiple skill challenges to complete--with scores assigned to each. The NFL winner was given a $50,000 prize to donate to the charity of his choice, while the winning golf pros were given cash prizes and exemption into the 2014 PGA and LPGA tours. Doleman's Team Blue was the only undefeated team in the competition and remained so until the finals, eventually finishing second to Team Red led by former 49er Jerry Rice.
In addition to occasional television appearances on sports talk shows such as Showtime's Inside The NFL, Doleman currently serves as an ambassador and on-air personality for Anthem Media Group's FNTSY Sports network. His commentary can also be heard on Sirius XM's Fantasy Sports Radio Channel.