Matt May was born into a water skiing family... a true "Ski Baby" and all-around water sports athlete. His mother Judes Gilkerson and his Uncle (Hall of Famer) Skip Gilkerson were seasoned show skiers at Cypress Gardens and the Tommy Bartlett show in Lake Delton, Wisconsin.  Before the age of two, Matt was skiing professionally at the Tommy Bartlett show under the tutelage of his Uncle Skip.  

Matt progressed quickly in his skiing skills.  He was slalom skiing by age four as well as barefooting and ski jumping by the age of five.     Although adept in competitive skiing, Matt’s bread and butter was the show skiing stage.   From 1986 to 1989 Matt was a featured skier at all of the Pro Tour events performing barefoot and freestyle jump exhibitions in front of thousands of fans each weekend.  In 1992, at the age of 16, Matt completed one of the most unique placements in the history of the sport.  He placed 3rd in the nation in freestyle jumping, traditional jumping, and barefoot jumping.

Matt has water skied for shows around the world, from the USA to Japan, Singapore, Germany, France, Russia, and Monaco.  Over a career spanning four decades, Matt May has had one of the most unique careers in the history of show skiing and in the sport of water skiing.  He has done a combination of things that no other skier in the history of the sport has achieved. His career as a show skier is unmatched.  

Many great skiers have come before Matt, but none have exceeded his diverse resume.  He was named Tommy Bartlett Skier of the Year 1998 & 2000: Sea World “Lynn Novakofski” Skier of the Year 1990, Boys Barefoot Jump National Champion and Record Holder 1995,  Collegiate All American Men’s Jump 1996-98, National Freestyle Jump Champion 1998,  5th place Wakeboarding Nationals 1998,  X Games Finalist Barefoot Jump 1999, Most valuable skier, Nagasaki Japan 2007,  Sea World Australia Skier of the Year 2012-2013, and Australian Men’s O35 Jump Champion.