Raven joined the World Wrestling Federation (WWF) as manager Johnny Polo, a spoiled, rich preppy kid, and was placed with Adam Bomb for 4 months until he was replaced by Harvey Wippleman. He was also manager of The Quebecers tag team, whom he led to three reigns as WWF Tag Team Champions. He occasionally wrestled, worked as a color commentator and co-host of Radio WWF, and, behind the scenes, worked as the associate producer for Monday Night Raw. Raven left in 1994.
Raven returned to the WWF in 2000 at Unforgiven when he interfered in the Strap match between Tazz and Jerry Lawler, by hitting Lawler with a DDT. His previous run in the WWF as Johnny Polo was ignored by the company. He then started teaming with Tazz before they went their separate ways. On December 22, 2000 in Chattanooga, he defeated Steve Blackman for the WWE Hardcore Championship, his first of a record 27 title reigns, though most of Raven's title reigns were short-lived. The Hardcore title at the time was contested under the "24/7" defense rule, leading to segments where one wrestler would win the title only to immediately lose it to another wrestler. At WrestleMania X-Seven, he competed in his only WrestleMania match, losing the Hardcore Championship to Kane in a Triple Threat match that also included The Big Show. At Backlash, he lost to Hardcore Champion Rhyno in a hardcore match. A brief angle had an anonymous Black Ninja, who was later revealed to be Tori aiding Raven in retaining the Hardcore Championship.
When the Invasion storyline began, he found himself in the new Alliance. His most notable storyline during this time, was when he was managed by Terri Runnels and destroyed the love interest of Saturn, his mop called "Moppy." He also started teaming with Justin Credible in late July 2001. By the end of the year, Raven was not seen on WWE programs, as the Alliance lost the "Winner Take All" match at Survivor Series.
In March 2002, when the WWE Brand Extension was announced, Raven was drafted to Raw. On the final SmackDown! before the split began, he defeated Maven to once again win the Hardcore Championship, thus bringing the title to Raw. He lost the title that Monday to Bubba Ray Dudley. At that time, Raven decided to spend some time announcing, and Raven became the new color commentator for Sunday Night Heat and Excess. This role lasted a couple of months, as he later quit the show to resume his wrestling career on Raw. This did not last long either, as was banished from Raw after losing a match to Tommy Dreamer on June 24, 2002. Raven was forced to spend the rest of the year on Heat. Although Raven did win his way back onto the Raw roster, he only had one match (losing to Jeff Hardy in a Royal Rumble qualifier) before being released from WWE the following week on January 20, 2003.