"21 Questions" is a song performed by American rapper50 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 Dirty Swift of Midi Mafia and samples elements from Barry White's "It's Only Love Doing Its Thing". The song is also known as the "big dropper" due to the fact it dropped from the top slot of the Hot 100 in its last week as number one down to number fifteen, making it the first song in Billboard Hot 100 history to fall from the top slot out of the top 10. The next week it dropped to 32 and then 2 weeks later it dropped completely off the Hot 100. This was the only single from the album to not have the Parental Advisory sticker on its cover since the only profanity was the word "nigga" in the first verse.
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".
On April 15, 2003, the video debuted on MTV's Total Request Live at number six, reached number one two days later, and stayed on the chart for 50 days. It also reached number two on the MuchMusic video charts.
"21 Answers" is a remix by Lil' Mo and former 106 & Park co-host Free, which was released as an 'answer track' to "21 Questions." Kevin "Dirty Swift" Risto, one-half of Midi Mafia, originally penned the idea of creating a female response record; he immediately got in touch with R&B singer Lil' Mo and added former 106 & Park personality Free to the mix. The song then premiered on New York's Hot 97 radio station—resulting in numerous rotations on various radio stations around the country—and later debuted on Billboard Hot R&B/Hip-Hop Songs at number 77. Although the song went on to spend eleven weeks on the chart based solely on airplay, it failed to see a release on Lil' Mo's sophomore album Meet the Girl Next Door (2003), due to the song not being finalized in time to meet the album's deadline. However, because of Elektra Records' 2004 merging with Atlantic, the song appeared on the 2011 re-release of Meet the Girl Next Door.