Songfacts®:

• Inspiration for this song came when 50 Cent heard a romantic LL Cool J song, and the girl riding next to him was clearly enjoying it. This convinced him to write a song revealing his softer side and his appreciation for women - something that most gangsta rappers shied away from. The song finds 50 asking a girl if she would still love him even if he wasn't rich and famous.
• This samples a 1978 song called "It's Only Love Doing Its Thing," which was written by Jimmie and Vella Cameron. The Canadian producer Dirty Swift (Kevin Risto), who was half of the Midi Mafia production team, put the track together. He delivered the beat to an executive at Universal Music, which was trying to sign 50 Cent to a record deal. This executive passed the track on the 50, who put lyrics to it. When 50 signed with Dr. Dre's Shady/Aftermath label, he recorded the song for his first album.
• Nate Dogg sings the chorus on this song, which was Dr. Dre's idea (50 planned to do it himself). Nate had a great track record in this line of work, dating back to his 1994 Warren G. collaboration "Regulate," and continuing on the Snoop Dogg track "Never Leave Me Alone" and the Ludacris song "Area Codes."
• Released as 50 Cent's second single, this hit #1 in the US in May 2003, less than three months after his first single, "In Da Club," topped the chart. 50's label was planning to release a more uptempo song as his second single, but DJs were already playing "21 Questions," so it made sense to put it out.
• When this song hit, its producer Dirty Swift concocted an answer song (in the very literal sense) called "21 Answers," which he had the female rapper Lil' Mo record.
• We counted them up. "21 Questions" actually contains 23 different questions.
• In October 2025, 50 used artificial intelligence to create a Motown-flavored version of "21 Questions" and posted it to Instagram. Responses were mixed, with some saying it sounds hollow and even cheesy, while others love hearing a different side of the rapper. 50 pledged to use the technology to touch up other songs, including ones from his unreleased backlog.