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 People’s Champ, the major-label debut from the Houston rapper and former Number Ones artist Paul Wall, didn’t have a lot of surprises. When The People’s Champ came out in fall of 2005, I knew what to expect: Fun and goofy punchlines about cars and bejeweled mouthpieces, Texan slow-crawl beats, an ill-considered crossover attempt or two. That’s mostly what I got. But one thing about the album did catch me off-guard. On the deep cut “March And Step,” Lil Wayne came in with guest verse that just kept drawing me back in.
I’d known Wayne’s music for years, but I wasn’t prepared for how he attacked “March And Step.” Wayne sounded just slightly deranged, slurring hard and stressing his syllables in unexpected ways: “I’m tryna get somewhere like I ain’t never been nowhere/ They’d probably suffocate, tryna breathe this N.O. air.” I found myself rewinding that one verse again and again, basking in it. Something was developing here, and I needed to understand it. This was the moment when I first caught onto what had been happening for a minute already: Lil Wayne was going on a run.
Over the next couple of years, my puzzled interest turned into full-on fanatical devotion. Wayne had been around. He’d been signed at 12, famous at 16. We’d watched him grow up. In 2004, when Wayne called himself “the best rapper alive since the best rapper retired,” I’d laughed. A couple of years later, it seemed like Wayne was actually selling himself short with that line. He was entering some rarefied airspace, seeing colors that had never been seen and translating those colors to the rest of the world. He was existing on an interdimensional plane, and it was a thrill to watch him go.
After Tha Carter II came out in December of 2005, Wayne went two and a half years without releasing a solo studio album. In that time, though, Wayne probably made dozens of albums’ worth of music. That music came into the world in random YouTube leaks, in supernova guest-verse appearances, and in mixtapes. Many of my favorite albums in those years weren’t albums at all; they were the mixtapes where Wayne hijacked other rappers’ beats and then obliterated those rappers’ original tracks. This was when I was getting started as a music critic, and a lot of my critic friends thought I was bugging out at first. By and by, all of them got it. Meetups in East Village bars turned into excited dissections of the latest Wayne freestyle. We were watching greatness.
The rest of the world was watching, too. There was no roadmap for what Wayne was doing. This was an established rap star who seemed indifferent to the idea of releasing his own commercially available music but who was constantly making music anyway, trusting that music to find its audience. Eventually, the 2009 documentary The Carter showed Wayne’s process — a microphone rigged up in a hotel room so that Wayne could record whatever came into his head, even while touring. Even when he appeared half-conscious, Wayne was coming up with jaggedly brilliant little gems that he barely understood himself, verses that he would immediately forget about after recording.
Lil Wayne was existing in a state of constant flow. He was touching the infinite. Eventually, though, market realities came calling. Lil Wayne had to put out an album. When that album did arrive, it was the moment when all the goodwill from all that stray brilliance paid off commercially. Tha Carter III came out in 2008, and it sold a million copies in its first week. In the download era, people didn’t even think that was possible anymore; nobody had done it since 50 Cent three years earlier. In that moment, Wayne almost fell backwards onto the top of the Hot 100, earning crossover-hit status with a sloppily Auto-Tuned astral sex jam that was as weird as everything else that the man was making.
Lil Wayne is the most important rapper of the 21st century. Ever since Wayne’s miraculous mixtape run, every rap star of any note has been trying to accomplish some version of what Wayne did. Wayne’s method — the freestyled verses, the all-night studio sessions, the constant stream of new music — has become industry standard. At least two of the world’s biggest rap stars are Wayne’s proteges. Many of the others — Future, Young Thug, Travis Scott, Lil Uzi Vert, Lil Baby, even Kendrick Lamar — are his stylistic descendants. There is no artist who’s ever made me feel the way Wayne did when he was at his peak. Seeing the rest of the world catch on was one of the greatest thrills of my music-critic career.
Wayne’s ascension to rap godhood was truly unlikely, a one-in-a-million shot. Dwayne Michael Carter Jr. grew up poor, the son of a teenage mother, in New Orleans’ Hollygrove neighborhood. (Chicago’s “Hard To Say I’m Sorry” was the #1 song in America when Wayne was born.) Wayne’s father ran out on the family when he was a toddler. Later, Wayne dropped the “D” from his first name because he didn’t want anything to do with his biological father. Wayne was a gifted kid, but he dropped out of school when he was 14. His rap career had already started.
When he was 11, Lil Wayne met Bryan “Birdman” Williams, the co-founder of the local New Orleans bounce label Cash Money Records. Wayne could rap, and that’s all he wanted to do. Wayne would call Birdman’s answering machine and spit bars into it. Soon enough, Birdman signed Wayne to Cash Money. Wayne’s mother objected. She didn’t want him to have anything to do with rap. When he was 12, Wayne shot himself in the chest and almost died. For years, he said that the shooting was an accident. Later, he told the whole story: He’d attempted suicide because he couldn’t imagine a life that wasn’t devoted to music.
Wayne got his way and signed with Cash Money at 12. At first, Wayne, then known as Baby D, was one half of BG’z, a duo that also featured the almost-as-young Cash Money rapper BG. The BG’z released their album True Story in 1995, and the 13-year-old Wayne only rapped on a few of its tracks. For several, Wayne, out of respect for his mother, vowed not to cuss on records, though he had a pretty loose definition of “cuss.” Eventually, Cash Money put Wayne and BG together with Turk and former Number Ones artist Juvenile in a supergroup called the Hot Boys. They released their first album Get It How U Live! in 1997. (The Hot Boys’ only Hot 100 hit, 1999’s “I Need A Hot Girl,” peaked at #65.)
Cash Money established a huge regional following, and with Southern rap on the rise, major labels started sniffing around. In 1998, Universal signed a huge distribution deal with Cash Money. The first album that came out under that deal was Juvenile’s 400 Degreez, and it was a smash. Cash Money always presented itself as a tight and slimmed-down unit, and the rappers almost always appeared on each other’s big singles. Juvenile’s “Back That Azz Up,” a #19 hit that still stands as a party-starting classic, ends with the 16-year-old Lil Wayne croaking a couple of simple lines that would get stuck in my head for days at a time: “After you back it up, then stop/ Whuh-whuh-whuh drah-drop it like it’s hot.” Years later, on “Lollipop,” Wayne was still quoting those lines.
Wayne appeared on a whole lot of Cash Money hits: BG’s “Bling Bling,” the Big Tymers’ “#1 Stunna,” the Cash Money Millionaires’ group effort “Project Chick.” In 1999, a few weeks after his 17th birthday, Wayne released his own debut album Tha Block Is Hot. The LP went platinum, and its title track became Wayne’s first Hot 100 hit as lead artist. (It peaked at #72.) At the time, Wayne fit into Cash Money’s whole guttural-bounce style. He was the baby of his crew, and while there was plenty of personality in his nasal rasp, nobody thought of him as an all-time rap great in the making. Instead, Wayne was regularly upstaged by more-weathered Cash Money rappers like Juvenile and by in-house production genius Mannie Fresh’s frantically bleepy beats.
The Cash Money crew had a big moment. They toured arenas with DMX’s Ruff Ryders crew. They made hits. They caused hysteria. Lil Wayne got shot in the chest again in 2003. This time, he later explained, the shooter was “a female fan” who might’ve been angry when she wasn’t allowed onto the Cash Money tour bus. Wayne survived that shooting, and when Cash Money’s initial run cooled off, Wayne remained.
Juvenile and BG eventually split away from Cash Money, while Turk went to prison after getting into a shootout with police, but Wayne kept developing. His delivery got sharper and harder while maintaining a lunatic edge. His lyrics became looser, more playful. On a series of underground mixtapes with his Sqad Up Crew — tapes that I didn’t hear until years later — Wayne built up the relentlessly creative flow that would make him a transformational figure. In 2004, a newly emboldened Wayne released Tha Carter, the album where he claimed to be the best rapper alive since the best rapper retired. I didn’t take that line seriously, but Wayne was turning into a star. That album had “Go DJ,” which went all the way to #14. As lead artist, Wayne wouldn’t chart higher until “Lollipop.”
I thought that “best rapper alive” line was funny, but not everybody was laughing. At the time, there were tons of rumors that Jay-Z, the best-rapper retiree that Wayne referenced, wanted to bring Wayne to Def Jam. In an effort to keep Wayne at Cash Money, Birdman made Wayne the president of the label and gave him his own Young Money imprint. Around the same time, Wayne also proved himself as a potential crossover pop figure when he laid a scene-stealing guest verse on the 2004 Destiny’s Child single “Soldier.” (“Soldier” peaked at #3. It’s a 9.)
Wayne’s position as Cash Money president was mostly ceremonial, and he wasn’t too involved with the label’s day-to-day business. But Wayne did attract some serious talent to Cash Money; two of his proteges will eventually appear in this column. Wayne was also increasingly close with Birdman, to the point where he referred to Birdman as his father. This was a deeply homophobic rap era, and a photo of Wayne kissing Birdman on the lips kicked off a mini gay panic. Eventually, Wayne and Birdman released the 2006 collaborative album Like Father, Like Son, and they got to #21 with the great single “Stuntin’ Like My Daddy.”
By the time Wayne released Tha Carter II at the end of 2005, I was an evangelist. I love that album. I reviewed Tha Carter II for Blender, and I had to listen to the album on a stereo in a record-label office, since they wouldn’t let me take it home. When I sent in my review, the editor wanted to know if I really thought it was a four-star album. Within a year, that same editor was writing magazine features about Wayne’s greatness.
After Tha Carter II came out, I tried to land a Wayne interview for months, and it seemed like that crusade was going nowhere. Then, one afternoon, I got a call telling me Lil Wayne would be calling me in 15 minutes. I was not ready. I spent most of that interview gushing, which Wayne didn’t seem to mind. I’d especially fallen for the Carter II track “Shooter,” a collaboration with future Number Ones artist Robin Thicke. That song sounded like a smash to me.
On the phone, I told Wayne that he should release “Shooter” as a single, that it could be his “Hard Knock Life.” The 1998 single “Hard Knock Life (Ghetto Anthem)” had turned Jay-Z into a crossover figure, someone who was known outside of rap circles. (“Hard Knock Life” peaked at #15, which is not, to my mind, an accurate representation of its cultural impact.) Wayne knew exactly what that meant, and he was excited about it: “Hey, man, that’s the whole shit. Me and my homies, we sit around, and even with the success of this album, we still sit and say I need that ‘Hard Knock Life’ song. I need that song that got Jay over, that ‘Hard Knock Life’ song!”
Lil Wayne eventually did release “Shooter” as a single, and it was not his “Hard Knock Life.” The song didn’t even make the Hot 100. Shows what I know. Still, Tha Carter II went double platinum, which made it Wayne’s biggest album yet. The great single “Fireman” made it to #32. At that point, Wayne was appearing on hits from tons of different artists: Chris Brown, Fat Joe, DJ Khaled, Lloyd. When I saw Wayne hop onstage at a 2007 Jay-Z show, he sang his hook from “Duffle Bag Boy,” a #15 hit from the Atlanta duo Playaz Circle, and the full-room singalong was deafening. I wonder how Jay felt in that moment.
When Jay-Z came out of his fake retirement in 2006, he might’ve been surprised to discover that he was no longer the best rapper alive. Wayne made it definitive when he freestyled over Jay’s 2006 comeback single “Show Me What You Got.” (“Show Me What You Got” peaked at #8. It’s a 5.) Wayne’s freestyle effortlessly gave Jay’s song a spike piledriver through a stack of flaming tables. Jay had to know that Wayne was crushing him, but he kept it classy. Jay and Wayne collaborated a few times and did a short tour together. I saw one of those shows, and Jay was much better live. Wayne was learning to play guitar, and he felt like he had to demonstrate his newfound skills to everyone. This was a bad idea. When it came to rapping, though, nobody was touching Wayne — not even Jay-Z. So it was a little shocking when Lil Wayne’s “Hard Knock Life” turned out to be a song without any real rapping.
“Lollipop” isn’t really a rap song; it’s more like miasmic sex-funk electro. The beat came from Jim Jonsin, a Miami producer who’d already made hits with artists like Trick Daddy and Jamie Foxx. (Jonsin is in the “Lollipop” video; he’s the white guy with the goatee playing keyboard.) Jonsin, like Polow Da Don, had a knack for translating Southern rap into pop. He made the “Lollipop” beat during a session with Danity Kane, the girl group that Diddy assembled on his Making The Band reality show. Jonsin produced Danity Kane’s biggest hit, the 2006 Yung Joc collab “Show Stopper,” which peaked at #8. (It’s a 6.) But when Jonsin played the track that would become “Lollipop” for the group, they weren’t interested. He took it elsewhere.
Miami’s Pretty Ricky were another group who had a lot of success working with Jim Jonsin. In their heyday, Pretty Ricky were the horniest boy band on the Scream Tour circuit. I saw Pretty Ricky on one of those Scream Tour shows, and their entire act seemed to consist of humping the stage, vigorously, at varying speeds and in varying states of undress. Thousands of teenage girls were watching this and losing their minds. It was a real eye-opener. Like: People are just living lives that I’ll never be able to comprehend. In 2005, Pretty Ricky got to #5 with the Jonsin-produced “Grind With Me.” (It’s a 7.)
When Danity Kane rejected the “Lollipop” beat, Jim Jonsin took it to Pretty Ricky leader Marcus “Pleasure P” Cooper, who was launching a solo career. (Jonsin co-produced Pleasure P’s highest-charting solo single, 2009’s “Boyfriend #2,” which peaked at #42.) Pleasure P was working with songwriter Stephen Garrett, better known as Static Major. Static, a Kentucky native, got his start alongside Timbaland and Missy Elliott in Swing Mob, the production crew run by Jodeci’s DeVante Swing. (When Static Major was born, Bachman-Turner Overdrive’s “You Ain’t Seen Nothing Yet” was the #1 song in America.) For years, Static worked closely with Tim and Missy, co-writing massive hits like Ginuwine’s “Pony.” (“Pony” peaked at #6 in 1996. It’s a 10.) Static also led the R&B group Playa, and they got to #38 with the Timbaland-produced 1998 single “Cheers 2 U.”
Beyond that one minor hit, Playa never had too much success. Static Major mostly remained behind the scenes, co-writing Timbaland-produced tracks like Aaliyah’s chart-topper “Try Again.” When Static heard Jim Jonsin’s beat, he came up with the basic idea for “Lollipop” on the spot. “Lollipop” has a bunch of credited songwriters, including Sean “The Pen” Garrett, a guy who’s been in this column a lot of times. Most everyone, though, agrees that Static Major was the main writer behind “Lollipop.” At Pleasure P’s suggestion, he and Jim Jonsin took the track to Lil Wayne.
“Lollipop” would’ve already been a weird song even if it had gone to an artist way less bugged-out than Wayne. Jonsin’s synth arpeggio is dazed and weightless — pretty in its own strange way. Static Major sings about his dick as a lollipop, which is not a particularly original image. (50 Cent had gone to #1 with “Candy Shop” three years earlier.) But Static’s melody is soft and eerie and ingratiating. The song makes sex sound strange and psychedelic, and nobody in 2008 was doing strange and psychedelic better than Lil Wayne.
I don’t even know how to accurately describe what Lil Wayne does on “Lollipop.” He’s not really rapping, but he’s not really singing, either. Instead, he’s chanting. He’s intoning. He’s giggling and sputtering and howling — all through the robotizing Auto-Tune that T-Pain had turned into a vehicle for hit songs. Wayne comes up with his own weird little melodies on “Lollipop.” He cracks up at his own jokes. He moans a line about “lovely lady lumps” with such fervor that I know he means it.
“Lollipop” is a dirty song. In the track’s storyline, Wayne meets a woman, and there’s in instant attraction: “Lil mama had a swag like mine.” Things escalate quickly: “Man, I ain’t never seen a ass like hers/ That pussy in my mouth had me lost for words.” She’s got a boyfriend, but he can’t do this, and he don’t do that. She needs to get a refund. She needs to bring his ass back. Instead, she and Wayne find themselves in the middle of the bed, give and getting head. Wayne also adds that “when I’m at the bottom, she Hillary Rodham,” and I still don’t know what that means.
“Lollipop” came out at the end of the ringtone era, when most of the tracks that reached #1 were clean and linear, whether they were recorded in million-dollar studios or in a teenager’s bedroom. That’s not how “Lollipop” works. Instead, “Lollipop” seems to emerge fully-formed from some kind of nebulous drug-fog. It sounds like a lube-slick dildo floating through the Crab Nebula. It sounds like an orgy on one of Saturn’s moons. It sounds like mystery. Lil Wayne and Static Major sing the song together, but neither anchors the other. Instead, the two of them find the same feeling, and they get lost.
At the beginning of “Lollipop,” Wayne murmurs the phrase “no homo.” I wish he didn’t do that, but I understand why he did. In that moment, most of the rap songs about sex sounded cold and clinical. “Lollipop” does not. Wayne oozes ecstatically all over “Lollipop.” He sounds like he’s having a religious experience, like he’s transcending some earthly plane. There’s vulnerability there, and this was a rap climate where a whole lot of listeners identified vulnerability as something to be eradicated. Most rappers in that moment used “no homo” as a quick punchline. For Wayne, it’s a broad disclaimer. He says it once, and then he disappears into his own euphoria. Even when the song breaks down, when the synth lines disappear, it’s so Wayne can murmur, “Call me, so I can make it juicy for ya.” His nastiness takes on cosmic dimensions.
Deezle, a producer who was working with Wayne a lot at the time, remixed “Lollipop,” punching up the drum sounds and giving it a serious low-end. That’s as crucial as anything else. While Wayne and Static vibe out together, those kicks and claps land hard enough to break your ribs. I think those drums are part of the reason why this post-Funkadelic oral-sex head-trip works as something that you might want to play loud in your car. I heard “Lollipop” coming out of a lot of car windows. (Later on, both Deezle and Jim Jonsin accused Cash Money of stiffing them on royalties. They weren’t the only ones. Cash Money’s reputation for ripping off producers is legendary, but I don’t put that on Wayne.)
“Lollipop” was divisive. People who doubted Lil Wayne’s supremacy used that song as ammo. This guy was supposed to be the world’s best rapper, but now he was singing like T-Pain on his big single? This for-the-ladies bubblegum club song? They didn’t get it. I wrote about “Lollipop” at the time, and what I said then still holds up now. “Lollipop” wasn’t a full representation of what Lil Wayne could do, but it was still a whole lot weirder than anything you’d hear from anyone else. Lil Wayne continued to operate without an inhibiting switch. Whatever song Wayne made, he lived that song.
In any case, the world still had plenty of opportunities to hear Wayne rap his ass off. That’s what Wayne did on “A Milli,” the other advance single from Tha Carter III. “A Milli” does everything that Wayne opted not to do with “Lollipop.” Over producer Bangladesh’s yammering beat, Wayne just loses his mind, rapping with near-devilish glee. Virtually every rapper on the planet freestyled over the “A Milli” beat in the summer of 2008, and none of them managed to outdo Wayne. (“A Milli” peaked at #6. It’s a 10.)
The Carter III rollout was an exciting time. On Christmas 2007, Wayne released The Leak, an EP of would-be Carter III tracks that didn’t make the album just because they leaked early. Some of those songs are absolute classics. (“I’m Me,” holy shit.) Wayne followed that with “Lollipop” and “A Milli,” and he sent the hype cycle into overdrive. The “Lollipop” video was giddy fun: Lil Wayne and Static Major putting on disheveled tuxedoes to board a giant limo full of women, flying down the Las Vegas strip to some kind of outdoor swimming-pool performance. In the middle of the clip, Wayne jumps on the roof of the moving limo to play a butt-rock guitar solo. The solo is not great, and it doesn’t appear on the single or album versions of “Lollipop.” But I love that Wayne gave himself a Slash-outside-the-chapel moment in a video that absolutely did not call for one.
The “Lollipop” video is dedicated to Static Major, who did not live to see its release. In February of 2008, Static Major died suddenly of respiratory distress after being hospitalized for an autoimmune disorder. Static was 33. When we’re talking about lead artists, there are six who have scored #1 hits after dying: Otis Redding, Janis Joplin, Jim Croce, John Lennon, Biggie Smalls, XXXTentacion. When you include featured guests, that list grows to eight. Soulja Slim died before Lil Wayne’s fellow Hot Boy Juvenile took “Slow Motion” to #1, and Static died before “Lollipop” ascended the charts. Static spent most of his career as a behind-the-scenes figure, and there’s something so sad about him not living to see the success of his own biggest hit.
For the “Lollipop” remix, Lil Wayne got together with Kanye West, who clearly understood the challenge of jumping on a Lil Wayne track in 2008. Kanye, in his new melodic Auto-Tuned style, absolutely went off on the remix, directly addressing the difficult proposition of going toe-to-toe with Wayne: “It’s a song with Wayne, so you know it’s gon’ melt! But you ain’t finna murder me like everybody else! I’ma rap like I got some type respect for myself! I don’t do it for my health, man, I do it for the belt!”
Kanye did his best, but Lil Wayne still murdered him like everybody else. In a couple of freewheeling remix verses, Wayne made one baffling decision after another. He called himself a “greedy mother-fudge-cake.” He advised you to use a latex because “you don’t want that ‘I think I’m late’ text.” He tells us that he’s the shit because he’s leaving skidmarks on everywhere he sits. “I’m in your neighborhood, area, CD thing, tape deck, iPod, your girlfriend, and she say I got great sex.” Kanye, the other biggest rap star of that moment, did everything in his power to stand tall next to Wayne, and he still couldn’t get there.
I saw Wayne and Kanye perform the “Lollipop” remix together at Summer Jam, and I watched that dynamic repeat itself. Wayne’s whole performance was absurd in the best way; I have vivid memories of him humping the stage while rapping an endless version of his cunnilingus anthem “Pussy Monster” over nothing but some human beatboxing. Kanye performed after Wayne, and he had a huge, expensive set built just for this one show. But Kanye noticed that he wasn’t getting the same reactions as Wayne, and he talked about it nonstop. Again and again, Kanye said that this was Wayne’s year, that he’d take it like a man. He told the crowd that this loss made him want to get back into the studio so that he could make something colder. Later that year, Kanye released 808s & Heartbreaks, so I guess it worked.
Tha Carter III couldn’t possibly live up to all its expectations. The album was too messy, too unfocused. It had some great moments and some weird ones, but it wasn’t the cohesive masterpiece that some of us wanted. Still, the album did massive numbers. It was platinum in a week, and it’s now platinum eight times over. Wayne’s third single, the T-Pain collab “Got Money,” made it to #10. (It’s a 7.) I know this isn’t really what happened, but I like the idea that so many people bought Tha Carter III just to show gratitude for Wayne releasing all those amazing free mixtapes online.
After Tha Carter III, things got weirder. In 2010, right near the peak of his career, Wayne had to serve a one-year sentence on Rikers Island for gun possession. Just before he started his sentence, Wayne released Rebirth, which was his attempt at a rock album. It was terrible, but it still went platinum. “Prom Queen,” its biggest hit, peaked at #15.
Wayne released another album, the much better I Am Not A Human Being, while he was still locked up. That album featured a few appearances from Drake, Wayne’s newest protege; that guy will appear in this column many times. Even with Wayne locked up, the Drake collab “Right Above It” made it to #6. (It’s a 6.) After Wayne got out of jail, he released the much-anticipated 2012 LP Tha Carter IV, which sold almost another million copies in its first week. That album’s biggest hit was another Drake collab, the #3 hit “She Will.” (It’s another 6.)
Over the next few years, Wayne continued to enjoy tremendous success, both on his own and with his Young Money crew. But Wayne’s records were increasingly scattershot, and he seemed like he was high all the time. I was worried about him. In 2012 and 2013, Wayne suffered a series of seizures that forced emergency plane landings, and I really thought the guy was about to die. He didn’t. Instead, Wayne got really into skateboarding, and he fell out with Cash Money. The label refused to release Wayne’s reportedly-finished Carter V, and Wayne resorted to releasing albums like the Tidal exclusive Free Weezy while battling Cash Money in court.
Wayne finally settled his business with Cash Money and released Tha Carter V in 2018. The album was a huge success that sent four songs into the top 10 and reminded a whole lot of us just how much we loved Lil Wayne. There’s been more weirdness since then, too. In 2016, Wayne appeared to endorse Donald Trump’s presidential campaign. It turned out that he was just playing the long game. Wayne had a federal gun charge hanging over him, and in 2021, on his last day in office, Trump gave Wayne a presidential pardon — just one more baffling chapter in Wayne’s baffling career.
Wayne has continued to record, sometimes approaching the glory of his peak. Right now, Wayne is on tour, and he’s apparently performing peak-era mixtape tracks that he’s almost never done live. Just a few weeks ago, Wayne released a greatest-hits album with a haphazard tracklist and one absolutely sick new track, the Swizz Beatz production “Kant Nobody.” On that track, Wayne proves that he is still nasty as hell: “Yes, mama, I’ma eat you like Jeff Dahmer! Say she on her period — let’s make a mess, mama!” (“Kant Nobody” peaked at #66.)
At this point, “Lollipop” is Lil Wayne’s only #1 hit as lead artist. It’s unquestionably Wayne’s biggest song. Just a few months ago, the “Lollipop” single finally went diamond, and Wayne celebrated the achievement on Instagram. But Wayne never stopped guesting on other artists’ songs, and this column will eventually cover a couple of singles with Lil Wayne verses. Wayne is still active, and he could always score another chart-topper. I’m not going to rule out that possibility. Why would I? He’s the best rapper alive.
GRADE: 9/10
BONUS BEATS: Dozens of songs have sampled “Lollipop” over the years, and one of those songs will eventually appear in this column. The first person to sample “Lollipop” might’ve been occasional Wayne collaborator David Banner, who used that sample on his 2008 single “Shawty Say.” Here’s the video:
(David Banner’s highest-charting single, 2005’s “Play,” peaked at #7. It’s a 6.)
BONUS BONUS BEATS: Here’s Lil Wayne protege Nicki Minaj rapping over “Lollipop” on a 2008 mixtape track:
(Nicki Minaj will eventually appear in this column.)
BONUS BONUS BONUS BEATS: The Swedish indie-pop duo jj built their 2009 track “Ecstasy” on a “Lollipop” sample, and they did a beautiful job expanding on the original track’s psychedelic qualities. Here’s “Ecstasy”:
BONUS BONUS BONUS BONUS BEATS: Here’s Das Racist’s 2010 track “Shorty Said,” which uses the “shawty said” construction from “Lollipop” to talk about girls saying racist things to the members of Das Racist:
BONUS BONUS BONUS BONUS BONUS BEATS: The biggest chart hit from Lil Wayne’s 2018 comeback album Tha Carter V wasn’t even released as a single. It’s “Mona Lisa,” the story-song where Wayne and Kendrick Lamar weave a narrative about a treacherous woman who sets guys up for robberies. During that song, there’s a moment where a phone rings, and the ringtone is “Lollipop.” Here’s “Mona Lisa”:
(“Mona Lisa” peaked at #2. It’s an 8. Kendrick Lamar will eventually appear in this column.)
The Number Ones: Twenty Chart-Topping Hits That Reveal The History Of Pop Music is out now via Hachette Books. Buy it here and let it leak on the sheet of the tablet in your mind. (I do write shit. I do have time.)
