In 1993, Clemonds performed in Vic's lounge at the Dunes Hotel in Las Vegas, where he sang his novelty hit, "Don't Send Me No E-Mail Unless You're a Female". (TOS novel: The Rise and Fall of Khan Noonien Singh, Volume 2)
In 1994, Clemonds died after years of alcohol abuse. Prior to his death, he had made arrangements to be placed in cryostasis in the hope that someday advances in medical science would eventually be able to revive him. Clemonds figured it was a scam, but at least it meant that his ex-wives would not be getting his money. His frozen remains were placed on board a spacecraft with several other individuals - including Ralph Offenhouse and Clare Raymond.
The spacecraft eventually drifted out of Earth orbit, and the solar system as well. In 2364, the USS Enterprise-D encountered the spacecraft containing the frozen bodies. Only the bodies of Offenhouse, Raymond, and Clemonds were intact - the bodies of the others had decayed during the long journey. Lt. Commander Data and Lieutenant Worf brought the bodies back to the Enterprise, where Doctor Beverly Crusher thawed them out. Beyond his name and occupation, there was very little Data was able to retrieve from the computer systems on board the spacecraft regarding Clemonds. Crusher noticed that Clemonds had a number of medical problems.
While Clemonds and the others were being revived, the Enterprise began to travel to the Romulan Neutral Zone to confront a Romulan D'deridex-class warbird. Of the three 20th century humans, Clemonds seemed to have the easiest time adjusting to 24th century life. When he tried to get medication from Dr. Crusher, she refused on the grounds that he had no medical need. Bored because there was no TV, he asked Data what people on the Enterprise did for entertainment. Data helped replicate a guitar for him, and Clemonds proposed that they find a couple "low mileage pit woofies" and get a party going.
Clemonds later became a popular entertainer and ushered in a revival of late 20th and early 21st Century popular music, performing throughout the Federation and becoming known for going to obscure starbases and Planetside bases to entertain Starfleet personnel who were in distant postings, not unlike American entertainers of the 20th and 21st centuries who visited troops in war zones. Clemonds also shed his addictions to drinking and substance abuse. (DTI novel: Watching the Clock)