In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
The crucial 1999 tome ego trip’s Book Of Rap Lists dedicates half a page to a self-explanatory concept: “Potholes In My Album: 17 Bumpy Songs On Otherwise Bumpin’ LPs.” You get it. In rap, just as in every other genre, a great album can have a song that doesn’t meet the standard of the rest of the record: “Chinese Arithmetic” on Eric B. & Rakim’s Paid In Full, “Mamacita” on Outkast’s Aquemini, that kind of thing. I don’t agree with plenty of ego trip‘s selections; tracks like Biggie’s “Respect” and Snoop Doggy Dogg’s “Who Am I (What’s My Name)” are incredible. But that’s still a useful framework for evaluating a particular track’s place in the universe.
You really couldn’t ask for a debut album more cohesive and complete than 50 Cent’s Get Rich Or Die Tryin’. On that record, 50 understood exactly who he was and who he wanted to be. Before Get Rich, 50 had already established his image as a hungry, reckless tough guy, and Get Rich found ways to broadcast that image, to make it loom as something larger than life. 50 sweetens that persona with catchy singsong hooks and with monster singalongs like “In Da Club,” but he rarely breaks character. Dr. Dre and the other producers furnish 50 with tracks that sound just as massive as his persona. But there’s one glaring exception that sits near the end of the LP, practically begging to be ignored.
Before Get Rich Or Die Tryin, 50 Cent had spent years mercilessly deriding his Queens adversary Ja Rule as a fake gangster, a paper tiger who wanted nothing more than to make sickly-sweet pop love songs. When 50 became rap’s biggest star practically overnight, he effectively put Ja Rule’s hitmaking run in the dirt. With “21 Questions,” though, 50 shamelessly drew from the Ja Rule playbook. “21 Questions” is unreservedly and almost proudly soft. It’s 50 Cent’s version of puffball heartthrob rap, his take on the genre that LL Cool J invented 16 years earlier with “I Need Love.”
“21 Questions” is a strange take on the “Bumpy Songs On Otherwise Bumpin’ LPs” template. The songs named in that ego trip list might’ve been bad — opinions vary — but they weren’t bad on purpose. With “21 Questions,” though, 50 practically invited a large slice of his fanbase to press skip. “21 Questions” existed to accomplish certain things, to move 50 that much closer to world domination. Since “21 Questions” was a #1 hit, you can’t say that it didn’t accomplish its goals. But “21 Questions” also made it plain that 50 Cent was not the rapper that some of us wanted him to be.
Dr. Dre didn’t want 50 Cent to include “21 Questions” on Get Rich Or Die Tryin’. 50 later told MSNBC, “Dre was, like, ‘How you going to be gangsta this and that and then put this sappy love song on?’ But I told him, ‘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 explanation rings true. 50 Cent’s upbringing was cold and dangerous, and he had to learn how to be different things to different people. 50 has always been just as clear about the idea that he made “21 Questions” as a naked attempt to appeal to a female fanbase. He told MTV, “I really made that record because I was in a car and LL Cool J came on. The girl next to me was all into it. It was a soft record, but she was so into the record that I said, ‘I want to make something that makes girls respond like that to me.'”
For 50 Cent, insincerity was always a business tactic. 50 didn’t smoke weed, but he still rapped about weed on “In Da Club.” When asked about the discrepancy, 50 would cite some of the rappers who’d made a lot of money by rapping about weed: Cypress Hill, Method Man, Redman. Why would 50 limit his audience? Why would he rap about not smoking weed when positive mentions of weed made more financial sense? In a weird way, that mercenary mentality reinforced the whole 50 Cent persona. This guy chose Get Rich Or Die Tryin’ as an album title; he made it clear that getting rich was his main objective. 50 didn’t care about hypocrisy, and that cold-blooded mentality was what allowed him to relentlessly clown Ja Rule while coming out with a single that might as well have been a Ja Rule song.
It was probably happening years earlier, but I remember the early ’00s as the first era when rappers would claim that they weren’t really rappers. Guys like Jay-Z and Beanie Sigel would insist that they were hustlers, businessmen, not artists. They made great art, but they also played up the storyline that the great art was simply a means to an end. As record sales went into post-Napster freefall, rappers would happily tout their clothing lines as the real sources for their income. People have always made music to make money, but there has usually been a kind of unspoken rule that you didn’t talk about the money as the end goal. 50 Cent didn’t care about that rule. “21 Questions” was a clear sellout move, but the whole idea of selling out was consistent with the 50 Cent persona.
50 Cent had “21 Questions” before he signed with Eminem and Dr. Dre at Shady/Aftermath. In 2001 or 2002, when 50 was on his mixtape rampage, every major label was trying to sign him, and one of those labels was Universal Music. (In a way, 50 did end up at Universal Music; Interscope Records, the parent label of Shady and Aftermath, is part of the Universal corporate umbrella. In the current era, major labels have done so much consolidating that different branches of the same companies sometimes compete against each other in bidding wars.) Dino Delvaille, an A&R vice president at Universal, passed 50 a CD of beats from the Brooklyn-based production duo Midi Mafia, and one of those beats was the track that would become “21 Questions.”
Kevin “Dirty Swift” Risto, one half of Midi Mafia, had made the “21 Questions” beat. Dirty Swift sampled “It’s Only Love Doing Its Thing,” a 1978 track from the former Number Ones artist Barry White. (White’s original version of “It’s Only Love Doing Its Thing” never charted, but Simply Red’s 1989 cover of that song made it to #28. “It’s Only Love Doing Its Thing” writers Vella and Jimmie Cameron — not the one who directed Avatar — got songwriting credit on “21 Questions.”) Dirty Swift took the Barry White song’s opening guitar riff, cut it up into a repeating figure, and paired it with the Barry White track’s miasmic synth sound. That’s textbook rap sampling: You use a previously existing record, focus on a couple of elements, and build something minimal but distinct from those shards. Dirty Swift was surprised when 50 Cent wanted that beat, but 50 heard a hit.
50 Cent started writing his “21 Questions” lyrics based on the beat, and he used the track to build his own kind of love song. In Fred Bronson’s Billboard Book Of Number 1 Hits, 50 lays out the song’s concept: “I’m not currently in a relationship, so those are the 21 questions I would be interested in asking a woman now.” Depending on how you add up those questions, 50 probably doesn’t really ask 21 of them.
All of the questions on “21 Questions” are built around a similar theme. 50 Cent knows that he’s desirable at the moment. He’s rich, and he’s coming off a string of good luck. But if his luck changed, would his prospective partner still be there? What if 50 was locked up for 25 years? What if he worked at Burger King? What if he drove a shitty car? What if he got shot? Also, would the girl support him if he was out committing crimes? What if her father found out about how he makes money? You can see how these questions might matter to 50 in a previous era of his life.
Amidst all those concerns, 50 does a whole lot of flirting, and most of that stuff is pretty annoying and boilerplate: “In the bed, if I used my tongue, would you like that?/ If I wrote you a love letter, would you write back?” The one line from “21 Questions” that everyone remembers is this one: “I love you like a fat kid loves cake.” Is that a great line? Is that a terrible line? Is it somehow both great and terrible, simultaneously? Nineteen years later, the jury is still out. (Most kids love cake. 50 didn’t need to go with a damn Goonies stereotype.)
The part that nobody mentions is that the “fat kid loves cake” line comes after a whole detour about what the girl would do if 50 cheated on her: “If I was with some other chick and someone happened to see, and when you asked me about it I said it wasn’t me, would you believe me, or up and leave me?/ How deep is our bond if that’s all it takes for you to be gone?/ We only humans, girl, we make mistakes/ To make it up, I’ll do whatever it take.” So this relationship hasn’t even started yet, and 50 is already trying to figure out what’s going to happen after he cheats. That seems like a red flag.
50 Cent recorded “21 Questions” before signing his Shady/Aftermath deal. On the original recording, 50 sang the hook himself. Dr. Dre might not have liked the song, but he still mixed it, and he also brought in a longtime ally to replace 50 on the hook. Nate Dogg had been part of Dre’s camp since the early G-funk days, and he’d sung dozens of memorable hooks on dozens of rap songs. Nate Dogg never flourished as a solo artist, but he was a key supporting player in Dre’s takeover.
Nathaniel Dwayne Hale grew up between Long Beach, California and Clarksdale, Mississippi, and he learned how to sing in church. (When Nate Dogg was born, the #1 song in America was Zager And Evans’ “In The Year 2525.”) Nate dropped out of high school at 17, and he enlisted in the Marines. He served for three years, mostly in Japan. Eventually, Nate went AWOL and got a dishonorable discharge. He moved back to Long Beach, did some low-level drug-dealing, and formed a rap group called 213 with his friends Snoop Doggy Dogg and Warren G. (The Dogg family tree is a little mysterious. Some reports say that Nate Dogg is Snoop’s cousin, and others claim that they were high school friends. Since Snoop calls everyone “cuz,” I’m inclined to believe the latter. Either way, Snoop will eventually appear in this column.)
213 made a few demo tapes, and Dr. Dre started collaborating with Snoop after Warren G, Dre’s half-brother, played him one of those tapes. All three members of 213 participated in Dre’s landmark 1992 album The Chronic. That’s when the world first heard Nate Dogg’s slick, unflappable baritone. Nate didn’t rap, and he didn’t indulge in R&B histrionics. Instead, he sang with the chilled-out simplicity of a ’60s-vintage soul singer. When Nate was singing about fucking or gangbanging, he sometimes sounded colder than the rappers on the songs. Nate’s ignorantly catchy bit about “and ya even licked my balls” on Snoop’s 1993 track “Ain’t No Fun (If The Homies Can’t Have None)” — a song about the other kind of gangbanging — was Nate’s first signature moment. The contrast between the lyrical nastiness and the musical smoothness was genuinely funny.
Snoop Doggy Dogg signed with Death Row, but the label didn’t give contracts to Warren G or Nate Dogg, and 213 didn’t make a group album until the 2004 one-off The Hard Way. In 1994, though, Death Row released the Above The Rim soundtrack. On that album, Warren and Nate teamed up for “Regulate,” a hazy and beautiful story-song about killing and fucking. “Regulate” became a crossover smash, peaking at #2, and it won Warren G a Def Jam contract. (It’s a 10.)
Even after “Regulate,” Nate Dogg never became a solo star. Instead, he continued to play his position, singing hooks for Death Row artists like 2Pac. In 1998, Nate finally released his long-delayed debut, the double album G-Funk Classics, Vol. 1 & 2. The album didn’t sell, but one single, the Warren G collab “Nobody Does It Better” peaked at #18. As lead artist, Nate never charted higher than that.
When Dr. Dre reemerged triumphantly with his 1999 album 2001, Nate Dogg was a key part of the supporting cast. The outro of Dre’s #23 hit “The Next Episode” featured the most memorable vocal bit of Nate’s entire career: “Hey hey-aaay-ay! [Extended pause.] [Still pausing.] [Keep that pause going.] Smoke weed everyday.” In the years that followed, Nate’s buttery hooks showed up on more and more big singles: Yasiin Bey and Pharoahe Monch’s “Oh No,” Snoop Dogg’s “Law Low,” Fabolous’ “Can’t Deny It,” Ludacris’ “Area Codes.” None of those songs went top-10 on the Hot 100, but if you listened to rap radio, all of them were anthems. Nate Dogg was a consistent, comforting presence. Nate released two more solo albums in the early ’00s, and both of them disappeared completely. It didn’t matter. When Nate Dogg was on someone else’s song, that song would shine a little bit brighter.
In videos, with his heavy-lidded eyes and his ever-present derby, Nate Dogg always looked cool as hell. Beyond that, he never really had much of an image, and I was surprised to find out that there was a lot of turmoil in his personal life. In 1991, before his career took off, Nate was arrested for two cases of armed robbery; a jury let him off in 1996. Later, Nate was charged with kidnapping a girlfriend and setting her mother’s car on fire; those charges were eventually dropped. More charges followed: Gun possession, domestic violence, stalking. Nate Dogg’s presence on record might’ve been smooth, but his life sure seems chaotic.
“21 Questions” is the only #1 hit with a Nate Dogg hook. It’s not Nate’s best guest-vocal — not by a long shot — but he does lend some calm authority to the song. 50 Cent, meanwhile, somehow sounds smarmy and bashful at the same time. In the context of Get Rich Or Die Tryin’, where “21 Questions” arrives after 13 tracks of hardness, the song’s softness sounds like an affected pose. (It is an affected pose, but the hardness of those other songs probably is, too. Nobody is one thing all the time.) I would always skip “21 Questions” when it came up on the album. On the radio, “21 Questions” wasn’t entirely unpleasant, but it was totally forgettable. It skated right past me. Radio was where “21 Questions” took off; stations started playing the song before 50 had released it as a single. In the Bronson book, Dirty Swift says, “The amount of spins ’21 Questions’ was getting was doubling every week, and it was charting. It was #1 in Dallas before anybody was even working the record, so they had no choice.”
“In Da Club” video auteur Phillip Atwell co-directed the “21 Questions” clip with Dr. Dre and Damon Johnson. The clip opens with 50 Cent counting vast stacks of money while giggling, as the ridiculously gorgeous actress Meagan Good looks on. (Good had just finished up a stint on the Nickelodeon sitcom Cousin Skeeter; Brick and Stomp The Yard were still a few years away.) Cops bust in and arrest 50 before the song begins, and he spends most of the video in jail, beefing with Tyson Beckford and asking Meagan Good his 21-or-so questions on jail phone calls, across glass in the visiting room, or in the conjugal-visit trailer. It’s Alicia Keys’ “Fallin’” video with the roles reversed, and it’s a canny way to make 50 still seen tough even in the context of a love-song video.
“21 Questions” did what 50 needed it to do. Get Rich Or Die Tryin’ was the biggest-selling album of 2003, and it eventually went platinum nine times over. 50 spent that summer on a contentious co-headlining tour with Jay-Z. Snoop Dogg and 50’s G-Unit comrades jumped on a remix of another Get Rich track, the steel drum-laced “P.I.M.P.,” and that song peaked at #3. (It’s an 8.) For the rest of the year, 50 kept flooding the zone. That same summer, 50 also guested on former Number Ones artist Lil Kim’s “Magic Stick,” and 50’s presence on that song definitely helped push it to #2 even though he didn’t appear in the video. (It’s a 6.) 50 and Lil Kim, both enormous divas, quickly started feuding with each other. Before the year was over, 50’s G-Unit crew released their double platinum debut album Beg For Mercy. (“Stunt 101,” G-Unit’s highest-charting single as a group, peaked at #13.) 50 Cent will appear in this column again.
Nate Dogg never released another solo album after “21 Questions,” but he kept showing up on other people’s songs, and he usually sounded great. Nate made the top 10 one more time. He sang a hook on Eminem’s “Shake That,” a deeply forgettable #6 hit in 2006. (It’s a 5.) Nate’s presence was something that I probably took for granted. But Nate suffered two strokes in 2007 and 2008, and he didn’t record much after that. In 2011, Nate Dogg died of heart failure. He was 41. A lot of people have sung a lot of hooks since then, but nobody’s ever done it like Nate Dogg.
BONUS BEATS: In 2003, Dirty Swift produced Lil Mo’s “21 Questions” answer song “21 Answers,” which featured a verse from former 106 & Park host Free. Here it is:
(Lil Mo’s highest-charting single as lead artist, the 2001 Fabolous collab “Superwoman Pt. II,” peaked at #11. As a guest, Lil Mo got as high as #4 by singing on Fabolous’ 2003 hit “Can’t Let You Go.” That one is a 3.)
BONUS BONUS BEATS: At the end of the Beastie Boys’ 2004 single “An Open Letter To NYC,” Mix Master Mike scratched up 50 Cent’s “21 Questions” intro. Here’s the video for “An Open Letter To NYC”:
(The Beastie Boys’ highest-charting single, 1987’s “(You Gotta) Fight for Your Right (To Party!),” peaked at #7. It’s an 8.)
BONUS BONUS BONUS BEATS: Here’s UK rapper J Hus covering “21 Questions” with a live band and switching up the lyrics in a 2018 BBC Live Lounge session:
BONUS BONUS BONUS BONUS BEATS: Here’s Puerto Rican rapper Myke Towers’ video for his 2020 single “Girl,” essentially a Spanish-language version of “21 Questions” with reggaeton drums:
(Myke Towers’ highest-charting single, the 2020 Ozuna/Karol G collab “Caramelo,” peaked at #76.)
BONUS BONUS BONUS BONUS BONUS BEATS: Here’s Chicago rapper Dreezy’s song “21 Questions,” which tackles 50 Cent’s song concept from a female perspective and which came out earlier this year:
(Dreezy’s only Hot 100 hit, the 2016 Jeremih collab “Body,” peaked at #62.)
The Number Ones: Twenty Chart-Topping Hits That Reveal The History Of Pop Music is out 11/15 via Hachette Books. You can pre-order it here.