The duo of "Too Sexy" Brian Christopher and "Too Hot" Scott Taylor were originally a tag team known as Too Much in the World Wrestling Federation. They made an appearance at WrestleMania XIV in a tag team battle royal won by L.O.D. 2000. The team feuded with fellow light heavyweight wrestlers such as Taka Michinoku and aided Jerry "The King" Lawler (Christopher's father) in his feud with Al Snow. They also feuded with The Headbangers, The Oddities, 8-Ball and Skull and The Hardy Boyz.
In 1999, Christopher became Grandmaster Sexay, Taylor became Scotty Too Hotty (later spelled as Scotty 2 Hotty) and Too Much was rebranded as Too Cool, debuting on television during the June 13, 1999 episode of Sunday Night Heat. They originally remained villainous characters, but in late 1999, around the time Rikishi Phatu joined the team, they turned into fan favorites. Too Cool's new characteristic was that of hip hop fans, which saw the trio of Scotty 2 Hotty, Grandmaster Sexay and Rikishi Phatu dancing around the ring while lights flashed and dance music played, an act that quickly became very popular with fans. In addition to the wildly popular post-match dancing routine, several of Too Cool's signature moves became extremely popular with the fans, including Scotty 2 Hotty's The Worm and Rikishi Phatu's Stink Face.
A famous moment came when the trio were all participants in the 2000 Royal Rumble. Rikishi had eliminated all three entrants in the match thus far, leaving only him and Grandmaster Sexay in the ring. Rikishi looked as if he was about to throw Grandmaster Sexay out of the ring to eliminate him from the Rumble, but Scotty 2 Hotty entered the match next and convinced Rikishi to instead dance to their music while the Rumble match was still ongoing. At the conclusion of their dance segment in the middle of the Rumble, Rikishi surprised his teammates by delivering a double clothesline and throwing them both to the outside to eliminate them. Rikishi shrugged his shoulders and his partners accepted the elimination with a good humor; no dissension would arise between them. Soon after this, Christopher suffered an injury and while he was recuperating, Scotty won the Light Heavyweight Championship.
Too Cool received arguably their biggest push when they became embroiled in a feud against the McMahon-Helmsley Regime, mainly wrestling against D-Generation X members Triple H, "The Road Dogg" Jesse James and X-Pac, along with a feud against the Radicalz. Too Cool participated in several main events on television during this push, including a 10-man tag team match on Raw where Too Cool teamed with The Rock and Cactus Jack against Triple H, X-Pac and The Radicalz.
Too Cool's success would peak in the middle of 2000 when Scotty 2 Hotty and Grandmaster Sexay defeated Edge and Christian for the WWF Tag Team Championship on an episode of Raw is War on May 29, 2000, while Rikishi would defeat Chris Benoit for the Intercontinental Championship on the June 20 edition of SmackDown!.
Despite enjoying immense popularity among the fans, Too Cool began to fragment in late 2000 when Rikishi left the group after becoming a villain. In March 2001, Too Cool fully disbanded when Scotty was, in storyline, sidelined with a broken ankle caused by Kurt Angle. That same year, Sexay was released from the WWF. After returning, Scotty formed a new tag team with Albert that lasted until March 2002. Scotty would injure his neck in April 2002 and was inactive for over a year.
Rikishi would eventually become a face again and reunited with Scotty 2 Hotty, who returned after an eighteen month absence from a neck injury to compete on the SmackDown! brand in October 2003. Rikishi and Scotty 2 Hotty won the WWE Tag Team Championship on February 5, 2004 after defeating the Basham Brothers. Also around this time, the WWE briefly re-hired Grand Master Sexay, although he was on the Raw brand and had no interaction with Scotty 2 Hotty or Rikishi. They held the titles for a little over two months, including a successful title defense at WrestleMania XX, before losing the titles to Charlie Haas and Rico on April 22. Rikishi would be released from the company shortly after the title loss, while Scotty remained with the company until being released on May 15, 2007.
On the January 6, 2014 episode of Old School Raw, Too Cool reunited with Rikishi, defeating 3MB (Heath Slater, Drew McIntyre and Jinder Mahal) in a six-man tag match. This was the first time in over thirteen years that the trio were in a 6-man tag team match. Too Cool also appeared at NXT Arrival, challenging The Ascension for the NXT Tag Team Championship. The Ascension would prevail however, retaining the titles.