In 1990, Smiley competed at World Championship Wrestling's Starrcade event, teaming with Chris Adams against the team of Konnan and Rey Misterio, Sr..
In 1995 and 1996, he briefly competed in Extreme Championship Wrestling.
Smiley signed with World Championship Wrestling (WCW) in 1997, making his debut on the October 13, 1997 episode of WCW Monday Nitro, defeating La Parka in a dark match. Smiley made his televised debut at the World War 3 pay-per-view, competing in the titular battle royal; however the match was won by Scott Hall. After being removed from television, he returned on the February 8, 1998 episode of Nitro, with a new gimmick, which saw him perform his signature dance move, the "Big Wiggle". However, in his return match, he would be defeated by Konnan. On the June 8 episode of Nitro, Smiley faced Fit Finlay for the WCW Television Championship, but failed to win the championship. At Fall Brawl, Smiley faced Ernest Miller in a losing effort.
Smiley turned heel in a backstage interview on the December 19 episode of Saturday Night, where he mocked the fans for saying his name incorrectly. At Starrcade, he defeated Prince Iaukea. He then feuded with Chavo Guerrero, Jr., on one occasion destroying Guerrero's hobby horse mascot, Pepè, by feeding it into a wood chipper on the January 11, 1999 episode of Nitro. At Souled Out on January 17, Smiley defeated Guerrero. In late 1999, Smiley entered the hardcore division. He would enter into a tournament to determine the inaugural WCW Hardcore Champion, which he won by defeating Brian Knobs in a tournament final at Mayhem on November 21. During his run with the championship, he would adopt the nickname 'Screamin', due to constantly screeching in a high-pitched tone during his matches, because of his fear of weapons. He would also often wear protective sports equipment as he entered the ring, usually also in the uniform of a local pro or collegiate sports team to gain a cheap pop. He lost the Hardcore Championship to Brian Knobs on the January 12, 2000 episode of Thunder, which he failed to regain at Souled Out in a fatal four-way match also involving Fit Finlay and Meng.
Smiley feuded with Brian Knobs, Meng and Terry Funk during his tenures as WCW Hardcore Champion, recruiting Chris Jericho's former associate Ralphus to be his manager. With the assistance of Ralphus, he stole a backyard wrestling championship from a group of children during a vignette.
Smiley remained in WCW until the company was sold to the World Wrestling Federation in March 2001. He was not hired by the WWF following the sale.
In 2012, when NXT became WWE's developmental territory, Smiley was hired as a trainer.