An Olympic Gold-Medal winning horse, Calypso was ridden throughout his illustrious career by Melanie Smith Taylor. The 16 hand and ½ inch Dutch gelding won his first Grand Prix, the prestigious and challenging American Jumping Derby in Newport, RI, at the age of six. It was then that Calypso provided a preview of what was to come-being named to two United States Olympic teams, a win at the World Cup Final and many major Nations' Cup and Grand prix wins.

In 1980 Calypso, or "Lyps" as he was called around the barn, carried Taylor to the Reserve Championship in the World Cup Final at Baltimore. Shortly thereafter, they were selected to compete on the U.S. Olympic Team scheduled to travel to Moscow. When the United States decided to boycott those Games, the United States Equestrian Team created a European tour instead. On this tour, Calypso earned top honors in the Grand Prix of Paris and at the Horse and Hound Cup at Wembley, as well as helping the U.S. team win the Nations' Cup in Dublin. The tour concluded with the "Alternate" Olympics in Rotterdam where the young horse carried Taylor to the individual Bronze Medal.

In 1982 Calypso and Taylor emerged as World Cup Champions, winning the Final at Gothenburg, Sweden. Later that year, the pair helped the U.S. team to a fourth place finish at the World Championships in Dublin, Ireland. Calypso also carried Taylor to a tenth place finish individually, the top U.S. finish in the Championships. That same year, Calypso and Taylor won two legs of the Triple Crown of Show Jumping-the American Invitational and the American Gold Cup-which, along with their earlier Jumping Derby win, made them the only horse/rider combination ever to win all three Triple Crown events.

Calypso and Taylor turned in yet another great World Cup performance in 1983, this time finishing third. Facing an injury that year after helping the USET win the Nations' Cup in Calgary, Canada, Calypso was rested for the remainder of the year. By 1984, he was fully recovered and went on to anchor the USET's Gold-Medal winning team at the Los Angeles Olympic Games. In 1984 and 1985 he won the richest show jumping purses to date in the $150,000 and then $200,000 Grand Prix, in Culpeper, VA. In 1988 the Dutch horse with tremendous talent, a big heart, and a brilliant mind was retired to Taylor's Tennessee farm where he lived in contentment until his death in December 2002.