Okerlund started his career in the American Wrestling Association (AWA) in 1970, where he occasionally filled in for ailing ring announcer and interviewer Marty O'Neill, eventually becoming O'Neill's permanent replacement by the end of the decade.
He stayed with the AWA until the end of 1983, when he was one of many AWA personnel to join the expanding World Wrestling Federation (WWF). He stayed with the WWF for nine years as their top interviewer and was host of such WWF shows as All-American Wrestling and Tuesday Night Titans.
In 1984, Okerlund and Hulk Hogan faced Mr. Fuji and George Steele in Minneapolis. He was supposed to stay on the apron and let Hogan fight, but when Hogan gave him a high five, the referee mistook it for a tag. Okerlund had to go in, but before his opponent touched him, he quickly got out of the way and tagged Hogan back in. Okerlund pinned Mr. Fuji for the victory.
Okerlund appeared at SummerSlam 1993 and made his final WWF appearance on the September 18, 1993 edition of Superstars. He then left the WWF entirely when his contract expired.
He debuted for World Championship Wrestling (WCW) on the November 6, 1993 edition of WCW Saturday Night. Three years later, his contract expired with WCW and he was off television for two months in the fall of 1996. His final appearance was at WCW Fall Brawl on September 15, 1996. Okerlund had talks with the WWF during this time, however, they could not come to terms. Mike Tenay took over special interviews and pay-per-view reports. Okerlund signed a new contract with WCW and returned on the November 11, 1996 edition of WCW Monday Nitro. Okerlund wrestled twice in WCW. The first was in mid-2000 when he and Buff Bagwell faced Chris Kanyon and fellow announcer Mark Madden, with Bagwell and Okerlund winning. However, Madden wanted Okerlund back in the ring the next week in a one on one match-up. The two did wrestle again and Okerlund won the match with the assistance of Pamela Paulshock. After that, he was with WCW until January 2001.
Shortly before WWF's purchase of WCW in 2001, Okerlund rejoined his old promotion (renamed WWE in 2002). His first assignment back with WWF was the Gimmick Battle Royal during WrestleMania X-Seven on April 1, 2001, along with Bobby "The Brain" Heenan. He hosted WWE Confidential in 2002, which lasted for two years. Okerlund also hosted WWE Madison Square Garden Classics, a weekly series featuring classic WWE matches that took place at Madison Square Garden from the last four decades. He's also the host for the WWE Classics On Demand Hall of Fame section, which takes a look at a different WWE Hall of Famer each month.
Okerlund was inducted into the WWE Hall of Fame on April 1, 2006, by Hulk Hogan.
In June 2008, Okerlund began hosting WWE Vintage Collection, a program which showcases archive footage from the extensive WWE video library. Okerlund conducted the interviews on the three-hour "Old School" episode of Raw on November 15, 2010, where he interviewed John Cena, Randy Orton, members of The Nexus and Mae Young in similar fashion as to how interviews were done in the 1980's.
On April 10, 2012, during the WWE SmackDown: Blast from the Past, Okerlund teamed with World Heavyweight Champion Sheamus, in a winning effort, against the team of Daniel Bryan and Alberto Del Rio. On the December 17, 2012 edition of WWE Raw, Okerlund appeared alongside Jim Ross and Ricky "The Dragon" Steamboat to announce the winner of the Slammy Award for Match of the Year. On March 4, 2013, Okerlund appeared at the second Old School Raw for Mae Young's 90th birthday party which was interrupted later by CM Punk. On January 7, 2014, Okerlund made an appearance at the third Old School Raw, in which he made references to the premium rate "wrestling hotlines" of the 1980s and 1990s. Also in 2014, Okerlund was part of the WWE Network original series Legends' House.
In November 2016, Okerlund became the narrator for the WWE Network original animated series WWE Story Time.
On January 22, 2018 at Raw 25 Years, Okerlund made his final WWE appearance where he interviewed AJ Styles.
Okerlund passed away on January 2, 2019.