Garland began attending shows at the Cumberland County Civic Center in Portland, Maine, helping the 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 the Survivor Series was taking place. In the same year, Garland began wrestling for the Massachusetts-based New England Wrestling.

In August 1991, Garland was introduced to the WWF by fellow NEW wrestler Phil Apollo. Garland made his first appearance with the World Wrestling Federation in October 1991 while still a junior in high school, teaming with Sonny Blaze and using the ring name “Scott Taylor”. Garland appeared sporadically with the WWF as an enhancement talent over the next six years, losing to wrestlers such as The Berzerker, Yokozuna and The Ringmaster.

Garland continued to attend college throughout his early tenure, and in 1994, he supplemented his income by working as a Fleet Bank bank teller and as the assistant manager of a Spencer’s Gifts outlet.

In 1997, Garland, now working for an insurance company, planned to wrestle tryout matches for Extreme Championship Wrestling. Upon hearing of his plans, President of the WWF Talent Relations, Bruce Prichard, signed him to a contract. Garland began wrestling in the 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, Taylor and “Too Sexy” Brian Christopher teamed together for the first time, taking part in a tag team battle royal. Following WrestleMania XIV, Taylor 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, Taylor adopted Christopher’s flamboyant actions and in-ring mannerisms and became known as Scott “Too Hot” Taylor, with the duo dubbed “Too Much”.

In June 1999, they were renamed “Too Cool” and given the characteristics of hip hop aficionados, delivering raps aimed at their opponents and parodying aspects of the hip hop culture.

Shortly after debuting their new gimmicks, the team was temporarily separated after Christopher tore his anterior cruciate ligament and was sidelined for five months. During this time, Taylor began incorporating breakdancing moves into his matches. In late 1999, Taylor was renamed Scotty 2 Hotty and Christopher was renamed Grandmaster Sexay. They aligned themselves with Rikishi Fatu (whom they quickly renamed Rikishi), forming a faction. Following their matches, they would dance in the center of the ring.

In early 2000, the group began feuding with The Radicalz, culminating with Too Cool teaming with Chyna to defeat Eddie Guerrero, Perry Saturn and Dean Malenko at WrestleMania 2000. After Grandmaster re-injured his leg, Scotty 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 for only 10 days before dropping it back to Malenko on April 27, 2000. Scotty challenged Malenko for the title once more at Backlash, but was defeated. Grandmaster returned in mid-2000, and on May 29, Too Cool defeated Edge and Christian for the WWF World Tag Team Championship with the assistance of rapper Joe C. They held the title until King of the Ring, when Edge and Christian regained the title.

Too Cool and Rikishi separated in late 2000 after Rikishi was revealed to have run over Stone Cold Steve Austin. Rikishi subsequently easily defeated his former allies in a handicap match. In February 2001, the intervertebral disc between Scotty’s C5, C6 and C6, C7 vertebrae bulged, and he was forced to take time off and do physical therapy 5 days a week. His absence was explained that he suffered a (kayfabe) broken ankle at the hands of Kurt Angle. While Scotty was recuperating, Grandmaster was released from the company for illegally conveying drugs across the Canada–United States border.

Scotty returned to the ring in June 2001, taking part in the rivalry between Team WWF and The Alliance. During this time, he formed a tag team with Albert, who subsequently adopted the nickname “The Hip Hop Hippo”, and they collectively became known as the “Zoo Crew”. The team competed in the tag team division until April 2002, when Albert betrayed Scotty by attacking him. Soon thereafter, Scotty began experiencing pains in his previously injured neck, and on May 7, 2002, Dr. Lloyd Youngblood performed neck surgery (cervical fusion) on him.

Scotty spent 17 months recuperating, returning to the ring on television in October 2003. Wrestling on the SmackDown! brand, Scotty formed a tag team with his former ally Rikishi. Together, they competed in the tag team division and ultimately defeated the Basham Brothers to win the WWE Tag Team Championship on February 5, 2004. Scotty 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, leaving Scotty on his own.

After Rikishi’s release, Scotty wrestled mainly on Velocity and in dark matches until early 2007. In April 2007 he returned briefly to the Raw roster, competing in a handful of matches on WWE Heat. He was released from the company on May 18, 2007.

After leaving WWE, Garland worked two shows for Puerto Rico’s International Wrestling Association (IWA) in mid-June 2007. He then wrestled on the independent circuit, working for at least 31 promotions in 11 countries as Scotty 2 Hotty and Scotty the Hotty. On December 6, 2014, Garland, as Scotty 2 Hotty, made his debut for the Japanese Pro Wrestling Noah promotion, teaming with Funaki and Super Crazy in a six-man tag team match, where they defeated Pesadilla, Yoshinari Ogawa and Zack Sabre, Jr., with Scotty pinning Pesadilla for the win.

Garland appeared in-character, alongside Kid Kash in the December 2009 video for the Irish band, Fight Like Apes’ single “Do You Karate”. In 2010, he completed filming a movie called Ultimate Death Match 3, which also featured other wrestlers. In 2017, the American music group, Migos, paid homage to Garland’s WWE character with their song titled “Too Hotty”.

In February 2013, Garland began training as a firefighter. In June 2013, he graduated from the Lake Tech Fire Academy in Florida. He subsequently began training as an emergency medical technician.

On September 7, 2016, Garland returned to WWE as a trainer at the WWE Performance Center.

According to Pro Wrestling Torch in 2017, Garland teaches the middle class at the WWE Performance Center, the second of four levels of classes.