Songfacts®:

• DJ Jazzy Jeff & the Fresh Prince specialized in goofy, self-deprecating story songs like "Girls Ain't Nothing But Trouble" and "Parents Just Don't Understand." Often, they find the Fresh Prince pursuing a bad idea, with predictable results. In this song, he decides to take on heavyweight boxing champ Mike Tyson in the ring, and it does not go well. After he takes his whoopin', Jazzy Jeff decides to take a crack at the champ.
• When this song was released, Mike Tyson was 37-0 and seemed invincible. The song peaked at #58 on December 9, 1989. On February 11, 1990, he fought his next bout, losing in a stunning upset to Buster Douglas, a 42-1 underdog. Tyson never regained his form, and in 1992 was sent to prison on rape charges. He resumed his boxing career when he got out in 1995, but lost two fights to Evander Holyfield, the second of which he bit off a chunk of Holyfield's ear.
  
  "I Think I Can Beat Mike Tyson" was perhaps the peak of Tyson's unrelenting hype before his fall. He had transcended his sport to become a media sensation, but he was clearly troubled and his issues were amplified by the unrelenting press coverage. Years after hanging up his gloves, he was welcomed back to Hollywood as a curious cameo, famously appearing in the 2009 film The Hangover.
• Tyson and his manager Don King appear in the video, which opens with the Fresh Prince running up the steps at the Philadelphia Museum of Art, site of a famous scene in the 1976 movie Rocky where the title character trains. In Rocky III, Rocky has won the title and spends much of his time making public appearances and doing endorsements. This detracts from his focus, and he loses the title to a hungry challenger (Clubber Lang, played by Mr. T). Tyson followed a similar path: instead of focusing on his next fight, he was preoccupied with other pursuits like this video.
• The Fresh Prince is Will Smith, who put some meat on his bones and starred as Muhammad Ali in the 2001 film Ali. He looked a lot more confident in the ring for that one.