Garland began attending WWF shows at the Cumberland County Civic Center in Portland, Maine, helping the WWF ring crew to construct the wrestling ring. After an independent promoter saw Garland wrestling with his friends, he offered Garland a job. In his first match, Garland wrestled Steve Ramsey in a Portland armory on November 23, 1989, the same night as Survivor Series.
In the same year, Garland began wrestling for the Massachusetts-based New England Wrestling Association. Between August 19, 1989 and November 4, 1993, Garland won the NEWA Tag Team Championship on two occasions with Steve Ramsey and the NEWA Heavyweight Championship on five occasions, feuding with wrestlers such as Rick Fuller. In August 1991, Garland was introduced to the World Wrestling Federation by NEWA wrestler Phil Apollo.
In 1997, Garland, by now working for an insurance company, planned to wrestle try-out matches for Extreme Championship Wrestling. Upon hearing of his plans, then-WWF Vice President of Talent Relations, Bruce Prichard, signed him to a contract. Garland began wrestling in the burgeoning WWF Light Heavyweight division as Scott Taylor. In late 1997, he took part in an eight-man tournament for the vacant WWF Light Heavyweight Championship, but was eliminated in the second round after being chokeslammed by Kane.
On March 29, 1998 at WrestleMania XIV, Garland and "Too Sexy" Brian Christopher teamed together for the first time, taking part in a tag team battle royal. Following WrestleMania XIV, Garland and Christopher continued to team together on the WWF's syndicated Saturday wrestling shows, with Taylor playing the straight man to Christopher's over-the-top, egotistical antics. Soon Garland adopted Christopher's flamboyant actions and in-ring mannerisms and became known as Scott "Too Hot" Taylor, with the duo dubbed Too Much During matches, the two would express an overt amount of concern about each other's well-being, including a great deal of hugging and consoling, leading to homoerotic undertones in their characters. Though this behaviour was eventually abandoned, it was picked up later on by the tag team of Billy Gunn and Chuck Palumbo.
In May 1999, Garland was renamed Scotty Too Hotty (later changed to Scotty 2 Hotty) and Christopher was renamed Grand Master Sexay. Collectively known as Too Cool, Garland and Christopher were given the gimmick of wiggers, delivering raps aimed at their opponents and parodying aspects of hip hop culture. Shortly after debuting their new gimmick, the team was temporarily separated after Christopher tore his anterior cruciate ligament and was sidelined for three months. In late 1999, Too Cool aligned themselves with Rikishi Fatu (whom they quickly renamed Rikishi Phatu), forming a stable. Following their matches, Too Cool and Phatu would performed a dance routine in the centre of the ring.
In early 2000, the group began feuding with The Radicalz. After Christopher re-injured his leg, Garland briefly returned to the Light Heavyweight division, and on April 17, 2000, he defeated Radicalz member Dean Malenko to win the WWF Light Heavyweight Championship. He held the title until April 25, 2000, when Malenko regained the title. Garland challenged Malenko once more at Backlash 2000, but was defeated once more. Christopher returned in mid-2000, and on May 29, 2000, Too Cool defeated Edge and Christian to win the WWF Tag Team Championship with the assistance of rapper Joe C. They held the titles until June 25, 2000, when Edge and Christian regained the titles.
Too Cool and Phatu separated in late 2000 after Phatu was revealed to have run over Steve Austin, with Phatu subsequently squashing his former allies in a handicap match. In February 2001, the intervertebral disc between Garland's C6 and C7 vertebrae bulged, and Garland was forced to undergo surgery. His absence was attributed by the WWF to a broken ankle suffered at the hands of Kurt Angle. Whilst Garland was recuperating, Christopher was released from the WWF for illegally conveying drugs across the Canada–United States border.
Garland returned to the ring in June 2001, taking part in the rivalry between the WWF and The Alliance. During this time he formed an oddball tag team with Albert (who adopted the nickname The Hip Hop Hippo) known as the Zoo Crew. The team competed in the tag team division until April 2002, when Albert betrayed Garland by attacking him. Soon thereafter, Garland began experiencing pains in his previously injured neck, and on May 7, 2002, Dr. Lloyd Youngblood performed neck surgery on Garland.
Garland spent 17 months recuperating, returning to the ring in April 2003 and to WWF (renamed World Wrestling Entertainment - WWE) television in October 2003. Wrestling on the SmackDown! brand, Garland formed a tag team with his former ally Rikishi Phatu. Garland and Rikishi competed in the tag team division, defeating the Basham Brothers to win the WWE Tag Team Championship on February 5, 2004. Garland and Rikishi successfully defended their titles in a four way tag team match at WrestleMania XX. Their reign ended on April 22, 2004 when they were defeated by Charlie Haas and Rico. On July 16, 2004, WWE released Rikishi.
Throughout the following year, Garland wrestled largely on Velocity and in dark matches. In mid-2005, he formed a tag team with Funaki, with the duo competing in both the tag team and cruiserweight divisions. Throughout 2006, Garland wrestled largely in dark matches.
On December 10, 2007, Garland returned to the WWE for one night only, during WWE Raw's 15-Year Special Anniversary Episode. He took part in a 15 Year Flashback Battle Royal, and was in the final four, before being eliminated by Skinner, however he did successfully perform his finishing move “The Worm” on Irwin R. Schyster
He now headlines house shows at the Plainfield gymnasium in Plainfield, CT. It was in Plainfield's Town Hall on March 1, 2008 where Garland became Eastern Pro Wrestling's heavyweight champion, defeating Bob Evans. Evans won the title back in a cage match on May 17, 2008 in Danielson, Connecticut.
In June, Garland appeared at the CLASH wrestling (Collective League of Adrenaline, Strength, and Honor) NPCI tournament, in which the first ever World Tag Champions would be crowned, and teamed with CLASH Champion Cameron Skyy. The team lost in the first round to Tommy Tydie and J. Miller. In August 2008, Garland changed his ring name simply to "Scotty" for Eastern Pro Wrestling matches. On October 3, 2008, Garland teamed with Owen Graichen in a loss to Fred Curry and Chris Venom in which the loser of the fall was forced to leave EPW for 60 days. Garland lost the fall, but was contractually obligated to wrestle Hingham, Massachusetts fireman Chris Dinapoli(himself with in-ring pro wrestling experience) the next night, but it was changed to a tag team match with Garland and Dinapoli defeating Jonny Idol and Nick Steele. Garland had to start his 60 days away from EPW after that match.