"21 Questions" is a song performed by American rapper 50 Cent and Nate Dogg. The song was written by 50 Cent, K. Risto, J. Cameron, and V. Cameron for 50 Cent's commercial debut album, Get Rich or Die Tryin' (2003). Released in 2003 as the album's second single, it became his second number one song in the United States, after "In Da Club". It reached #6 on the UK Singles Chart while "In Da Club" was at No. 23, giving him the rare feat of having two singles in the Top 30 at the same time. The track was produced by Chris styles and samples elements from Barry White's "It's Only Love Doing Its Thing". This was the only single from the album to not have the Parental Advisory sticker on its cover. The song was mixed by Dr. Dre.

When producer Dr. Dre worked with 50 Cent on his debut album, he did not want the song on the album. According to 50 Cent, "Dre was, like, 'How you goin' to be gangsta this and that and then put this sappy love song on?'" 50 Cent responded saying, "I'm two people. I've always had to be two people since I was a kid, to get by. To me that's not diversity, it's necessity."

The music video for "21 Questions" was directed by Damon Johnson, Dr. Dre and Phillip Atwell in March 2003. It depicts 50 Cent arrested and confined to prison, where he tries to keep in touch with his girlfriend, played by Meagan Good. In prison, he is constantly harangued by rival inmate (Tyson Beckford). The video ends with a continuation of the beginning, showing 50 Cent and his girlfriend watching from their home as the police arrest Beckford instead; the prison scenes are revealed to be a hypothetical scenario imagined by a worried 50 Cent. The video has cameo appearances by G-Unit and Nate Dogg, who sings the chorus and the outro. The video concept can also be originated from Nate Dogg's "Never Leave Me Alone".

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