Oliver grew up in South Florida and took his first dance class at the age of 2. He performed in Miami City Ballet's first Nutcracker, fell in love with both Tchaikovsky and ballet and migrated west to train at the San Francisco Ballet School.
In 2001, he began his professional dance career back on the east coast with the Boston Ballet.
A year later, he settled on middle ground in Texas. He joined Houston Ballet as a Corps de Ballet member in 2002 and rose through the ranks to First Soloist dancing 20 seasons with the company. He has danced a variety of classical, contemporary and character roles, performing in work by George Balanchine, Jiří Kylián, William Forsythe, Nacho Duato, Hans Van Manen, Christopher Bruce, Mark Morris, Ben Stevenson OBE, Stanton Welch, Justin Peck, Julia Adam, Aszure Barton and Jerome Robbins, among others. Oliver has choreographed for Houston Ballet, Dance Alive National Ballet, Houston Contemporary Dance company, Mercury Ensemble, the Texas Contemporary Art Fair, the Blaffer Museum, Houston Cinema Arts Society, the Museum of Fine Arts Houston, and Moody Center for the Arts. Alongside his good friends and fellow dancers, Melody Mennite and Connor Walsh, he created REACH, a platform for Houston dancers and choreographers to create new work while raising money for arts education.
He co-choreographed What we keep with Melody Mennite and Connor Walsh for Houston Ballet's performances at the George R. Brown Convention Center in 2018.
He debuted his first solo commission Following for Houston Ballet’s 50th Anniversary season in 2019. In May of 2023, he created an original production of Romeo + Juliet for the New Orleans Ballet Theatre where Oliver now is the resident
choreographer. He will premier a new production of Dracula for NOBT in May of 2024.