Born and raised in Cleveland, Oakley attended John Hay High School and Virginia Union University, a Division II historically black university in Richmond, Virginia. As a senior in 1984–85, Oakley led Division II in rebounding with an average 17.3 per game.
Oakley was drafted with the 9th overall pick in the 1985 NBA draft by the Cleveland Cavaliers, but his draft rights were traded to the Chicago Bulls. Oakley provided another scoring option and steady offensive and defensive performances to an up-and-coming Bulls squad led by Michael Jordan. He also assumed the role of the team "cop" whose duty primarily was to protect young Jordan against cheap shots and roughhousing tactics of opposing players. Oakley earned All-Rookie Team honors in 1986.
With the drafting and development of Horace Grant, the Bulls traded Oakley to the New York Knicks for 7'1" center Bill Cartwright. Oakley eventually became a part of the core which the Knicks built around, which also featured Patrick Ewing, John Starks, and point guard Mark Jackson. During the Knicks' 1994 season, which included a record 25 playoff games, Oakley started every regular season and playoff game for a record 107 starts in a single season. During his tenure with the Knicks, Oakley was primarily known as a defensive specialist.
In 1998, Oakley was traded by New York to the Toronto Raptors for blossoming star Marcus Camby. For the Raptors, he provided a veteran presence to a young team that included Vince Carter and Tracy McGrady.
In 2001, Oakley was traded by the Toronto Raptors with a 2002 2nd-round pick to the Chicago Bulls for Brian Skinner. This was his second tenure with the Bulls. Starting 36 of his 57 played games, he averaged 3.8 points per game, 6 rebounds per game, and 2 assists per game.
In 2002, Oakley signed as a free agent with the Washington Wizards. He was reunited with former teammate Michael Jordan. Oakley played 42 games during the 2002–03 season, averaging 1.8 points per game, 2.5 rebounds per game, and 1 assist per game.
The 2003–04 season was Oakley's last. On March 18, 2004, Oakley signed the first of two 10-day contracts with the Houston Rockets. Oakley only played 7 games, in which he averaged 1.3 points per game, 0.7 rebounds per game, and 0.3 assists per game. At the end of the season, Oakley retired from the NBA.
In 2007 Oakley was reported to be attempting an NBA comeback, at age 44. He claimed Dallas, Miami, Cleveland and New York were interested but said he would "not [come] back cheap".
On December 26, 2010, Oakley was hired as an assistant coach for the Charlotte Bobcats under then-head coach Paul Silas.
He left that position on December 1, 2011 after experiencing health issues with back pain, during the 2010–11 season.
Oakley owns several commercial enterprises, including:Hair Solutions and Nails EtCetera in east Cleveland, Ohio, "salons started with seed money from Oakley and run by his sisters"
Oakley's car wash, oil change, and detail centers in Brighton Beach, Brooklyn and Yonkers, New York
Oakley's Wash House, a combination car wash and laundromat Oakley founded in east Cleveland, Ohio, overseen by his sister Carolyn and mother Corine
Red, The Steakhouse, restaurants in Cleveland, Ohio and South Beach, Miami, Florida
Oakley was inducted into the Virginia Sports Hall of Fame and Museum in honor of his 19-year professional basketball career. The induction ceremony was held on April 30, 2016.
In September 2016, a portion of Deering Street in Oakley's hometown of Cleveland (near his alma mater of John Hay High School) was renamed Charles Oakley Way in his honor.He placed in the top ten in rebounds per game five times between 1987 and 1994 (second in 1987 and 1988).
Due to his durability he actually placed in the top ten in total rebounds 6 times and led the league in total rebounds twice (1987 and 1988).
In 1994, he became an NBA All-Star and was chosen to the league's All-Defense 1st team.
Oakley currently ranks 18th all-time in NBA games played with 1,282 games, and 21st all-time in career rebounds with 12,205 rebounds.
In 2011, Oakley filed a lawsuit against the Aria Resort and Casino in Las Vegas, alleging a group assault by five security guards employed by the casino on May 28, 2010. On July 30, 2016 Oakley married his wife Angela Reed.
On February 8, 2017, Oakley was involved in an altercation at Madison Square Garden as the Knicks faced the visiting Los Angeles Clippers. According to the Knicks, Oakley was ejected from the arena after he is alleged to have yelled at James L. Dolan, the Executive Chairman of Madison Square Garden and MSG Networks, and refused to stop, an allegation he denies. He was charged with three counts of misdemeanor assault and criminal trespassing. In a statement, the Knicks stated that Oakley "came to the game tonight and behaved in a highly inappropriate and completely abusive manner. He has been ejected and is currently being arrested by the New York City Police Department."
In response, Oakley claimed that he sat down in his seat and he saw the Knicks owner James Dolan look at him and within four minutes he was being asked to leave the arena. He says that he didn't become combative until he was asked to leave for no apparent reason. While admitting "I shouldn't have put my hands on anyone," Oakley disputed the Knicks' rendition of events in an interview with ESPN's "The Undefeated," which reported that Oakley says he "never said a word to Dolan" and "was minding his own business when he was confronted by Madison Square Garden Security, who asked why he was sitting so close to Dolan before demanding that he leave the building."
On February 13, 2017, NBA legend Michael Jordan and NBA commissioner Adam Silver met with both Dolan and Oakley at NBA headquarters. Oakley and Dolan both apologized for the fallout and both were currently negotiating a truce. "Both Mr. Oakley and Mr. Dolan were apologetic about the incident and subsequent comments, and their negative impact on the Knicks organization and the NBA," Silver said. The statement says Dolan hopes Oakley can return to MSG as his guest in the near future. On February 14, 2017, the ban from Madison Square Garden was lifted. On September 12, 2017, it was reported that Oakley was filing a civil lawsuit over the incident.