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 later migrated west to train at the San Francisco Ballet School. In 2001, he began his professional dance career back on the east coast with Boston Ballet.
A year later, he found his home in Texas, joining Houston Ballet as a Corps de Ballet member in 2002. Over the next 20 seasons, he rose to the rank of First Soloist, performing a wide range of classical, contemporary, and character roles. Oliver worked with celebrated choreographers such as 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.
In addition to his performance career, Oliver has established himself as a dynamic choreographer, creating works for Houston Ballet, Dance Alive National Ballet, Houston Contemporary Dance Company, and other prestigious organizations, including Mercury Ensemble, the Blaffer Museum, and the Museum of Fine Arts Houston. He co-founded REACH, a platform supporting new choreographic works and arts education, alongside Melody Mennite and Connor Walsh. Together, they co-choreographed What We Keep for Houston Ballet in 2018. In 2019, Oliver debuted his first solo commission, Following, for Houston Ballet’s 50th Anniversary Season.
Since transitioning into a new creative role, Oliver has become the resident choreographer for New Orleans Ballet Theatre (NOBT). In May 2023, he premiered an original production of Romeo + Juliet for NOBT. Following its success, he debuted a new production of Dracula in May 2024, solidifying his place as a leading voice in contemporary ballet choreography.