He was one-half of the tag-team Too Cool with Grandmaster Sexay and sometimes Rikishi. During his time in Too Cool, Garland won the WWE Tag Team Championship 1 time with Rikishi and won the WWF World Tag Team Championship with Grandmaster Sexay. He also defeated Dean Malenko to win the WWF Light Heavyweight Championship on April 17, 2000 but he held the title for only 10 days before he dropped it back to Malenko on April 27, 2000.