Charles gained a reputation for being a hard-worker and tenacious rebounder for all of the teams he played for, especially the Knicks, where Charles played the role of partner to Patrick Ewing in the low post. Drafted in 1985 by the Cleveland Cavaliers, Charles' draft rights were immediately traded to the Chicago Bulls. There, Oakley provided another scoring option and steady offensive and defensive performances to an up-and-coming Bulls squad led by a young Michael Jordan.

With the drafting and development of Horace Grant, the Bulls traded Oakley to the New York Knicks for 7'1" center Bill Cartwright. Oakley finally became a a share of the core using which the Knicks built in, which besides featured Ewing, John Starks, and point guard Mark Jackson. Charles' difficult function & physical play in the Knicks defense won the hearts of several firm Knicks fans, making him a fan special.

Inside 1998, Oakley became a single half of 2 controversial moves a Knicks manufactured for immature, when he was traded to the Toronto Raptors for 6'Eleven" forward Marcus Camby. The other move saw Starks go to the Golden State Warriors for Latrell Sprewell. On the Raptors, he provided a veteran presence to a young team led by Vince Carter and Tracy McGrady. Charles later played for the Bulls again, followed by the Washington Wizards and most recently the Houston Rockets. On the Rockets, Charles was briefly reunited with former Knick teammates Mark Jackson, who was the veteran point guard behind Steve Francis, and Patrick Ewing, who is an assistant coach with the Rockets.