On the July 11, 2005 episode of Raw, horror movie-style vignettes began airing to promote the debut of "The Boogeyman". After a few weeks, the vignettes were moved from Raw to SmackDown!, but the planned debut was delayed when he hyperextended both knees and needed time to recover. He made his World Wrestling Entertainment (WWE) debut on the October 14, 2005 episode of SmackDown!, being brought in by network executive Palmer Cannon as part of a "new talent initiative". The Boogeyman then proceeded to smash an oversized alarm clock on his own head. For the next few weeks, The Boogeyman appeared in unexpected places backstage (closets, vans, etc.), reciting different nursery rhymes and holding up clocks before screaming his catchphrase "I'm The Boogeyman and I'm comin' to get'cha!" and laughing maniacally.
At Survivor Series, The Boogeyman helped SmackDown! general manager Theodore Long defeat his Raw counterpart, Eric Bischoff. He made his official in-ring debut on the December 2 episode of SmackDown!, defeating Simon Dean in a squash. During this match, he took a handful of live worms from his pocket and stuffed them into his mouth. Over the next few weeks, Boogeyman's opponents were generally "flattened" in the ring, left with worms in their mouths and/or spit on their faces. His official pay-per-view debut was at December's Armageddon, when he came to the ring to confront Vito and Nunzio, who were dressed as Santa Claus and an elf.
Boogeyman's first major feud occurred with John Bradshaw Layfield (JBL) and his "fixer" Jillian Hall, and it began when he stalked the duo throughout a number of shows. During the January 6 episode of SmackDown!, he caught a fleeing Hall and shoved worms down the back of her skirt. On the January 13 taping of SmackDown!, during a Piper's Pit segment, The Boogeyman not only sniffed a "growth" on Jillian's face, but then licked it, bit it off and ate it. The Boogeyman faced JBL at the Royal Rumble, winning in under two minutes.
After defeating The Dicks in a handicap match on the February 24 episode of SmackDown!, The Boogeyman dumped a bucket of worms on the announce table, frightening special guest commentators Booker T and his wife Sharmell. The Boogeyman subsequently began to stalk Booker T and Sharmell over the next few weeks. He and Booker T were set to face off on the March 18 Saturday Night's Main Event XXXII, but the match was canceled due to Booker T faking a knee injury to escape competition. The feud eventually culminated at WrestleMania 22, with The Boogeyman defeating Booker T and Sharmell in a handicap match. During the match, Boogeyman kissed Sharmell with a mouthful of worms. The match had to be cut short because of a biceps tear at a house show. To explain his absence to rehab his injury, Booker T and Sharmell obtained a restraining order against The Boogeyman on the April 7 episode of SmackDown!.
As SummerSlam approached, The Boogeyman began appearing in television spots to promote the event. Vignettes also began airing advertising his return to SmackDown!. The Boogeyman returned on the October 27 episode of SmackDown!, attacking and spitting worms into the faces of The Miz and Kristal Marshall. During the feud, he again terrorized and stalked his opponents, and eventually ended The Miz's undefeated streak at the Armageddon pay-per-view on December 17.
The Boogeyman then feuded with Finlay, who ended The Boogeyman's undefeated streak when Hornswoggle interfered. On the February 2 edition of SmackDown! during a match against Chris Benoit for the WWE United States Championship, Boogeyman abducted Hornswoggle, distracting Finlay and giving Benoit a chance to win the match with a roll-up. On the February 16 edition of SmackDown! The Boogeyman appeared with a little person of his own, Little Boogeyman. His purpose was to counteract Hornswoggle, who was proving a problem in one-on-one matches with Finlay. The Boogeyman and the Little Boogeyman lost to Finlay and Hornswoggle in a mixed tag team match at No Way Out. The team lost a rematch the following week on SmackDown!; Little Boogeyman was pinned by Finlay, after Boogeyman had chased away Hornswoggle.
The Boogeyman returned to in-ring action when he teamed with Kane during his feud with William Regal and Dave Taylor. This also marked the return of Little Boogeyman. The feud would be short lived as Boogeyman and Little Boogeyman would then start another feud with Finlay and Hornswoggle. Boogeyman and Little Boogeyman were defeated in a mixed tag match by Finlay and Hornswoggle at Saturday Night's Main Event XXXIV on June 2.
The Boogeyman ended his tenure on SmackDown! with a loss to Mark Henry in a squash match, as part of Henry's new "Path of Destruction" gimmick. After that match, Mark Henry then beat up Little Boogeyman who was at ringside, and Henry gave him a body splash, severely injuring him.
On the June 11 edition of Raw, The Boogeyman was drafted to the ECW brand in the annual WWE draft. The next day, he debuted for the brand and defeated Matt Striker, beginning a feud with him. On July 10, in New Orleans, The Boogeyman was a guest during a Striker's Classroom segment, ostensibly to be educated on worms, only to be attacked by Striker's debuting enforcer, Big Daddy V. The Boogeyman was not seen for the next three weeks, finally re-emerging on the July 31 episode — with a new face paint design and black contact lenses — to scare Big Daddy V off after he finished a match. Boogeyman was taken out by Big Daddy V from behind after a distraction from Striker a week later.
On the August 14 episode of ECW, Boogeyman scored a disqualification victory over ECW Champion John Morrison after Morrison shoved the referee. The Boogeyman went on to successfully team with CM Punk at Saturday Night's Main Event XXXV on August 18 against Morrison and Big Daddy V. On the August 28 episode of ECW, Boogeyman was one of the participants in the fatal four-way match for a shot at Morrison's title; however, CM Punk was the victor. On September 4, on ECW, Boogeyman defeated Matt Striker by disqualification when Big Daddy V interfered, and went on to hit Boogeyman with a ghetto drop on the outside of the ring. On the September 18 episode of ECW, Boogeyman and Big Daddy V finally faced off in their first one-on-one match, which Boogeyman lost.
On the October 7 episode of ECW, a vignette was aired promoting The Boogeyman's return. Additional vignettes aired for a few weeks after that. On the October 13, 2008 edition of Raw, The Boogeyman made his return, appearing during a segment with Johnny Knoxville, Chris Pontius, and Big Dick Johnson, ending with The Boogeyman bringing live worms out of a bag and after putting them in his own mouth spat them into the mouth of Pontius.
The Boogeyman made his ECW return on the November 25 episode, in a segment with John Morrison and The Miz. He made his return to in-ring competition on December 9 against Scott Reed, a local talent, who he defeated with ease. On the December 30 episode of ECW, he lost to John Morrison and The Miz in a no disqualification match with Finlay as his partner. On the January 20, 2009 edition of ECW, he defeated Paul Burchill by disqualification, his first victory over a non-enhancement talent since returning to the brand. His last appearance on WWE programming was on the March 3 episode of ECW, where he lost in a match against Kane. The next day on March 4, 2009, WWE announced that they had released The Boogeyman from his WWE contract.
On the December 16, 2012 episode of Raw, the Boogeyman returned during the Slammy Awards, sneaking up on former rival Booker T.
Boogeyman appeared in Halloween-themed videos on the WWE YouTube channel in both November 2013 and October 2014. On the December 22, 2014 episode of Raw, Boogeyman appeared in a segment on the WWE App.
On January 25, 2015 at Royal Rumble, Boogeyman entered the Royal Rumble match as a surprise entrant at number seven, marking his first WWE in–ring performance in almost six years, but was quickly eliminated by Bray Wyatt. On November 6, it was announced that Boogeyman had signed a legends contract with WWE. On January 22, 2018, Boogeyman made an appearance on Raw 25 Years. On July 22, 2019, Boogeyman appeared at the Raw Reunion show, and scared Drake Maverick in the locker room, helping Pat Patterson pin Maverick and win the WWE 24/7 Championship.