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Five Burning Questions: Drake and Lil Durk Arrive at No. 2 on Hot 100 With ‘Laugh Now, Cry Later’

How should Drake feel about his No. 2 debut for "Laugh Now, Cry Later"? And how much of a triumph is the featured appearance for Lil Durk?

Drake has spent much of 2020 the way he spent a great deal of the previous decade — at or around the top of the Hot 100.

He’s already visited the chart’s top five four times this year: With Future collab “Life Is Good,” solo Dark Lane Demo Tapes advance cut “Toosie Slide,” DJ Khaled teamup “Popstar,” and now the Lil Durk-featuring lead single from his upcoming Certified Lover Boy album, “Laugh Now, Cry Later.” Unlike “Toosie Slide,” however, “Laugh Now” falls one spot short of debuting atop the Hot 100, landing at No. 2 behind the continuing cultural phenomenon that is Cardi B and Megan Thee Stallion’s “WAP.” 

How should Drake feel about the No. 2 debut? And how much of a triumph is the featured appearance for Lil Durk? Billboard staffers discuss these questions and more below.


1. “Laugh Now, Cry Later” debuts at a hearty No. 2 on the Hot 100 this week, but obviously fails to unseat Cardi B’s Megan Thee Stallion-featuring “WAP” phenomenon at No. 1. If you’re Drake, what are you doing at this news: laughing now, laughing later, crying now, or crying later? 

Rania Aniftos: I’m going to say crying now, because at this point I think Drake is too used to No. 1s, so a second place slot might come as a bit of a disappointment. I’m also going to add laughing later, because I’m sure even Drake has had “WAP” stuck in his head all week.

Josh Glicksman: Laughing later. Of course there’s the initial disappointment of not landing the No. 1 debut, but I think that Drake has gotten to the point in his illustrious career where he can step aside and appreciate the gravity of the moment that Cardi B and Megan Thee Stallion are currently enjoying. “Laugh Now, Cry Later” serves as a nice reminder to him that he’s still always just a moment’s notice away from becoming today’s must-listen material, which is all he really needed to do here, anyway.

Jason Lipshutz: If I’m Drake, I’m laughing later: sure, it’s probably a teensy bit frustrating to have “WAP” block a second straight No. 1 Hot 100 debut a few months after a Kenny Chesney album boxed Dark Lane Demo Tapes out of the top spot on the Billboard 200 chart. Fortunately, Drake has a mind-boggling amount of hits — now the most top 10 hits in the Hot 100’s history, as well as the most Hot 100 entries, period — so I can’t imagine getting too hung up on a No. 2 debut.

Dan Rys: I’d probably go with laughing now. I think that with all of Drake’s success it’s easy to forget how difficult it is to debut that high with a brand new song, and even if it didn’t conquer every single track in the country in its first seven days, it almost did. When you look at a song like “WAP,” it’s such a singular moment for two brilliantly creative rappers, both aesthetically and musically, that I think you just bow down and let them have their moment for as long as it lasts. After all, these two songs will both be going off in the club for years to come, and one’s success does not come at the expense of the other — they can both shine. That is, if clubs are ever allowed again. Wear a mask!

Andrew Unterberger: Crying now, though maybe just a single tear. The downside of being Drake, the gold standard for 2010s commercial success, is that anything but the top spot — especially for the lead single from a new project, with a shiny new celeb-cluttered video and everything — pretty much has to be seen as a disappointment. And given that Aubrey even snuck out a lyric video for this one before the final bell rung, it’s pretty clear that he was gunning for that No. 1. No shame in getting beaten by a historic hit in its second week, but maybe a little sting just the same.

2. Between “Life Is Good,” “Toosie Slide,” Dark Lane Demo Tapes, his two DJ Khaled collabs and now this song — with new album Certified Lover Boy still to come — it’s been a pretty busy 2020 for Drake. Do you think he’s established himself as being still at the top of the game for the new decade, or do you think that’s up to the new album to help him prove?

Rania Aniftos: So many rappers have been breaking in and taking over the scene in the past year, but I still think Drake has put in the time and delivered enough hits to remain a constant on the hip-hop throne. They don’t call him the 6 God for nothing, I guess.

Josh Glicksman: I don’t know that it was necessarily a point that needed re-establishing, but sure. Even with rappers like DaBaby and Lil Baby relishing lengthy stays atop the Hot 100 and Billboard 200, respectively, in 2020, Drake has already notched a No. 1 single, three more in the top five, and a fourth in the top 10 (with DJ Khaled on “Greece”), and a No. 2 debut on the Billboard 200 (Dark Lane Demo Tapes). Certified Lover Boy feels likely to add another No. 1 to the collection, but his rightful status among the top names in the industry has long been solidified.

Jason Lipshutz: It’s hard to imagine that Certified Lover Boy could underachieve to such a degree that Drake’s super-duper-stardom is called into question; if he’s going to fall off, it’s not going to happen this year. Even before his official follow-up to 2018’s massive Scorpion, he’s collected a No. 1 single in “Toosie Slide,” a handful of other top 10 hits, and now has a new single that might be the strongest of the bunch, with the commercial bow to demonstrate the enthusiasm around it. He has nothing to prove with Certified Lover Boy as one of the most successful musical artists ever — and of course, Certified Lover Boy is still probably going to be huge.

Dan Rys: Despite what social media might have you believe, two things can be true at once! I think both are accurate. There’s still no real challenger to Drake’s position at the top of the commercial hip-hop/R&B ladder at this point — other than maybe Travis Scott, though Drake makes it seem much more effortless (and maybe it is). At the same time, each new album — for any artist, really — should be pushing the form forward in some way, in my opinion. I won’t claim to be Drake’s biggest fan, but I will say that when he really puts his full muscle into a project, which I’m not sure he’s really done 100% since 2016’s Views, you can feel a cultural shift happening at the same time, and people tend to follow his lead.

I think if he does that again with his new album, and he’s certainly shown in the past that he can, then he’s off to the races in the new decade. Then again, with how the new decade has started, do you really want to be the poster child for it? This pandemic sucks!

Andrew Unterberger: He’s still near the top for sure, but there’s signs of slippage when it comes to his status as the unquestioned No. 1. “Toosie Slide” debuted atop the Hot 100 but slid out of the top 10 faster than I expected, while neither of the Khaled collabs from last month are currently in the top 20. He’s still putting up numbers that 99.999% of other rappers would give their left arm for, but it’s clearly not 2018 anymore, when three of his Scorpion singles topped the Hot 100 for a historic 29 combined weeks. If he wants to show he’s still on that level — which, to be fair, nobody stays at forever, or even for particularly long — he better have some real killers in reserve on Certified Lover Boy.


3. While charting in the Hot 100’s top tier is obviously nothing new for Drake, it’s the first visit to this territory for long-acclaimed Chicago MC Lil Durk. Does his relatively short guest verse on the track do him justice, or would you have liked to hear more from him? 

Rania Aniftos: Lil Durk has the skill for a longer verse, but he made the most of his time by throwing a few jabs in his lines. He’s also riding jet skis and having a blast in the music video, so I don’t think he’s too heated.

Josh Glicksman: Give me more Lil Durk! The Chicago MC shines throughout his nearly 30 seconds of rapping, taking the mic and running with it after a clean handoff from Drake to kick off the second verse. That said, I would’ve loved to hear the two pass it back-and-forth one more time, even if it only included a few more bars from Durk and another Auto-Tuned wail into the depths of the beat. Hell, even if it was just him riffing during the 45-second instrumental outro, I’d take that, too.

Jason Lipshutz: Good on Lil Durk for making the most of the biggest mainstream opportunity of his career and leaving his imprint on “Laugh Now, Cry Later” in a short amount of time. The song already barrels past the 4-minute mark, so extending his verse may have made his appearance less impactful; what we end up with is less than 30 seconds of compact bars, with an abrupt stop for Durk to moan for a second and switch up his flow.

Dan Rys: I’ve long been of the opinion that Durk was the most melodic and the best storyteller of all the MCs that emerged from the Chicago drill scene, even if others, like Chief Keef of course, proved to be more influential. Here he doesn’t really have the time to paint a full picture, but he’s still able to get across a lot in a short amount of time in his clear and concise way — look how quickly people jumped on his line about listening to rats in the club (what’s a club?!?!). So while I am generally disposed to wanting to hear more from Durk, I think what he does here fits the track (which is the most important thing anyway), and if it leads to more people getting interested in his catalog and going back and listening to what he really has to offer, all the better.

Andrew Unterberger: I’d have either cut one of Drake’s hook repetitions to give Durk more screentime, or just let Durk take the hook around the block one time himself. The most electric moment in the song is Drizzy’s handoff to his junior counterpart, so it would have been nice to hear the Chicago MC re-entering at least once more. But given that it’s Durk’s first visit to the Hot 100’s top 40, let alone the top five, he’s probably not complaining a ton.

4. “Laugh Now, Cry Later” obviously comes with a very fun new video that’s already been gif’d and meme’d half to death. What’s your favorite moment from the clip? 

Rania Aniftos: It’s the Druski2Funny pep talk and a teary-eyed Drake telling himself to have a “warrior spirit” for me.

Josh Glicksman: As much as it fills my heart with unbridled joy to see Kevin Durant dunking the ball and blocking shots with ease, the few moments of Drake soft tossing baseballs to himself never fail to make me laugh. To his credit, he does a great job poking fun at himself throughout the video, but this is the one scene that I can’t tell whether or not he’s trying to be serious. There’s no star-studded cameo, there’s no real development in the plot — it’s just Drake hitting lazy fly balls to no one in particular. Not particularly well struck balls, either: routine fly outs to very shallow center field, if I had to guess.

Jason Lipshutz: It’s midnight, the Nike Headquarters are deserted as Drake pulls up, he enters the basketball facility… and Kevin Durant is just waiting there for him in the dark, stone-faced and hat-clad! Is this how KD has been spending his rehab while the rest of the NBA toils away in the Orlando bubble? The first sports star cameo is the funniest, and segues into Durant half-heartedly trying to block a Drake jumper we never see land.

Dan Rys: I mean, Drake crying will always make me laugh. I enjoyed the fact that he can fully embrace how ridiculous some of the tics he returns to so often in his songs are, as when everybody looked into the camera saying “baby.” Also, I recently got into cars, so I rewound a few times (do people still say rewind these days?) to check out the Mercedes-Maybach concept cars which are nuts, and yes I will accept one for free please. “I’m just regrouping! I’m just regrouping!” reminds me of that classic @dril tweet: “I’m not mad. please don’t put in the newspaper that i got mad.”

Andrew Unterberger: I like the Drake emergence from the water and turn to the camera for the seemingly most-delayed “…baby” in the song. Very .gifable, certainly.


5. Give me one bold prediction about Certified Lover Boy — about what it will contain, who it will feature, how it will be received, what it will mean for Drake, anything. 

Rania Aniftos: If the album title is any indication, I think Drake will continue to be his passionate self. We’ll get the fiery verses that are going to blow up on TikTok, but we’ll also get his usual in-his-feels songs that fans know and love. As for features, it would be nice to see Drake add some more Lil Durk type-assists from hip-hop artists who haven’t gotten the mainstream attention they deserve yet.

Josh Glicksman: I’ll go with Drake giving listeners some behind-the-scenes snippet or voice memo from his son, Adonis. I wouldn’t count on it being particularly long — maybe even just a laugh or the audio from the clip of him saying “Dada” — but sign me up for an Adonis vocal credit.

Jason Lipshutz: After Scorpion featured a posthumous cameo from Michael Jackson on “Don’t Matter To Me,” I think we’ll see Drake get even bolder with a from-the-vaults guest spot that will pique the curiosity of fan and non-fans alike. Could Prince be next? How about The Notorious B.I.G., or Aaliyah, or David Bowie, or Whitney Houston? While I don’t have any insider information, I don’t think anything is necessarily off the table, either.

Dan Rys: One and a half hours of stand up comedy. He has to do it. He could do it. I wouldn’t even be mad. I’m not mad.

Andrew Unterberger: I’ll call back to our 5BQ from last month and say that yes, he does in fact get Madonna on a track this time around — and that the collab is about as well-received as their Coachella appearance together.