Crocker attended Earl Warren High School in San Antonio, Texas, his final three years of high school after attending William Howard Taft High School as a freshman. While attending Warren High he was a 2005 Texas Association of Basketball Coaches First-Team 5A All-State selection and named the 2005 San Antonio Player of the Year by the San Antonio Express-News in his senior season. He averaged 22.0 points, 10.0 rebounds and 4.0 assists per game as a senior and scored a career-high 44 points against Bowie High School his senior season. He earned all-city and all-district honors as a junior and recorded a triple-double as a junior against James Madison High School. He was coached by Jay Keller at Warren HS and by Mike Carillo at Taft HS.
Prep school
Crocker played prep school basketball after his senior year at Warren High. He spent the majority of his prep school career battling an ankle injury, but finished the season averaging 15.2 points, 5.0 rebounds and 3.0 assists per game for The Patterson School in Lenoir, North Carolina. Coming out of prep school he was rated as the No. 80 overall player in the class of 2006 by Rivals.com and ranked as the country's 18th-best shooting guard by Rivals and Scout.com. He was also rated as the 25th-best post-graduate prep school player in the country by HoopScoopOnline.com. At Patterson School he helped his team to a 34-3 record and a No. 3 national prep school ranking despite being limited to 10 games due to injury. At The Patterson School he was coached by Chris Chaney.
College
Crocker burst onto the scene at the University of Oklahoma where he was named to the starting lineup in his first collegiate game under new Oklahoma head coach Jeff Capel III. He scored 15 points in his first game and took off from there for the Sooners with several dunks over his freshman season. He ended his debut season at Oklahoma averaging 8.6 points and 3.7 rebounds per game. Near the end of the season he began to become comfortable at the collegiate level and the Sooners will rely upon him heavily in 2008-09 to take the team to the next level.
Professional career
Crocker played for the Houston Rockets in the NBA Summer League in 2010. In 2010, he signed with Albacomp in Hungary. On June 11, 2016, Crocker signed with Yeşilgiresun Belediye of the Turkish BSL for the 2015–16 season. On July 30, 2016, Crocker signed with Jilin Northeast Tigers of the Chinese Basketball Association. However, he left the club before appearing in a game for them, and on October 20, 2016, he signed with Turkish club Tofaş. On August 8, 2018, Crocker signed a one-year deal with Russian club BC Khimki. On July 19, 2019, he signed a two-year contract with Pınar Karşıyaka of the Turkish Basketbol Süper Ligi.