Quite a few music artists are in their flop era right now. Think about it: Drake hasn’t been the same since Kendrick Lamar knocked him out in their 2024 beef. Katy Perry once dominated the charts, but her recent releases haven’t been fireworks. And there was once a point where it felt impossible to step foot in a workout class without hearing Lizzo, but her latest album fizzled out. 

Some examples, in other words, are obvious. But what does it really mean for a song to flop? According to Tom Breihan, executive editor at StereoGum and author of the book The Number Ones Twenty Chart-Topping Hits That Reveal the History of Pop Music, it’s all relative. 

“There’s a million songs on Spotify that nobody will ever hear,” he told Vox. “Those songs are not necessarily flops because they did not necessarily come with expectations. When a major artist does not reach whatever benchmark they or their fans or their label expect for them, it can be embarrassing. People love to seize upon that embarrassment and take off running with it.”

Why do some songs flail while others succeed? And how does an artist bounce back from those unmet expectations? We find out that and more on this week’s episode of Explain It to Me, Vox’s weekly call-in podcast.

Below is an excerpt of my conversation with Breihan, edited for length and clarity. You can listen to the full episode on Apple Podcasts, Spotify, or wherever you get your podcasts. If you’d like to submit a question, send an email to askvox@vox.com or call 1-800-618-8545.

Are the songs that flop bad? Is that why they’re flopping? 

In some cases, yeah. You can definitely pick out a few and be like, “That wasn’t the one.”

A lot of it is just timing and luck. Sometimes an artist comes along at the exact right moment and builds up goodwill and puts out the right song for themselves. Sometimes they misread the room in sort of howlingly, clangingly obvious ways, and they end up not doing well. 

It’s happened to plenty of great people. Plenty of stars have bounced back from having flops, but it does happen. 

What are some really good songs that have flopped? 

As an online indie music critic, my prototypical example is Emotion by Carly Rae Jepsen. She had had this gigantic global breakout smash with the song “Call Me Maybe.” The album that she put out after this is this brilliant, layered, excellent pop record that became, I would say, influential upon the idea that you could be a pop star who was a cult artist, like an indie rock band or an underground rapper. But it didn’t sell. It didn’t do numbers. So in its moment, it was a critically beloved flop. 

How much of becoming a hit is about the music itself and how much of it is about virality and marketing? 

Those things are so bound up with each other. A lot of the time, artists are making songs that are engineered to go viral, or they’re making songs that comment on their own public perceptions. 

When someone like Lizzo comes along and puts out a record that doesn’t do well, it becomes a bigger story than just, “Oh, people weren’t feeling this song.” It becomes, “Oh, people don’t like this person,” or “This person has run out of goodwill.”

Like a Lizzo song: You hear her persona jumping through the speaker, whether the song does well or not. So the song and the artist become inextricable from each other. The song and the marketing become inextricable. 

There is another example of an artist who has gone from really high highs to very low flops that I would love to get into, and that’s Katy Perry. I feel like we’ve come a long way from Left Shark at the Super Bowl. What happened there? 

Katy Perry has had the career that pop stars used to have, where they have a crazy dominant stretch where they’re knocking out hit after hit after hit, and they’re unstoppable. Then everything kind of tails off over time. One album has five No. 1 hits. The next album has two No. 1 hits. The next album has no significant hits at all, but a couple top 10s. 

She put out an album right at the beginning of the pandemic. You can say, “Well, that one didn’t do well, and that’s not her fault.” Then she spent a long time on American Idol as a judge; she spent a long time playing Las Vegas residencies. And then she was like, “That’s it. I’m quitting American Idol. I’m coming back. I’m being the pop star that you all want me to be.“

She made a bad album. She also reunited with Dr. Luke, who was the co-writer and producer of lots of her big hits but who, in the time since she stopped working with him, accusations were made. Kesha, who was friends with Katy Perry when she came up, was the person making those accusations. So there’s a lot for the internet to glom onto there.

“Especially now, a song can debut at No. 1 based on streams and conversation, and then it can disappear from the charts.”

That’s how a song goes from being a bad song to a notorious flop — when not only does the song not perform, it actually burns up a lot of the goodwill that this person has had. 

What songs did everyone maybe expect to be huge, but then bombed? 

It is possible for a song to be a No. 1 hit and still a flop. Especially now, a song can debut at No. 1 based on streams and conversation, and then it can disappear from the charts. 

In 1996, Michael Jackson released “You Are Not Alone.” The song debuted at No. 1. It fell pretty quickly. The album didn’t do that well. The song ultimately is not remembered that well, and has really entered the notorious shadow zone over the years. 

Are there examples of songs that critics hated initially, and then over time became classics?

So many. The songs that were hits and were universally regarded as irritating in their time have a great hit rate. People were annoyed by “MMMBop,” by Hansen, or “Wannabe” by the Spice Girls. 

There were certainly critics who understood ABBA when they were popping off, but they were, I would say, widely regarded as a punchline. Now that is just an impeccable, beautiful, influential pop catalog. 

A song like the Quad City DJ’s “”C’mon N’ Ride It (The Train)” was not a song the critics were really lining up to praise in the 1990s, but as a person who was a child then, I can tell you that song goes so hard and never stopped going hard. 

What’s the biggest misconception people have about pop music success? 

I think the biggest misconception is the idea that a label or a corporation can engineer a giant hit. They can observe trends. They can put their money into promotion. But you never know what people are going to actually grab onto and what they’re not. 

There are things that they can do to create the impression that something is connecting, but you need to have real sustained success to have everybody be like, “Okay, no, this actually is huge.”

How do artists tend to respond if they’ve entered a flop era?

There’s a grand, beautiful history of artists who instead of trying the same thing over and over again, they become behind-the-scenes figures. They write songs for other people, or they produce, or they become managers. 

Max Martin, who is now ahead of John Lennon, but behind Paul McCartney in terms of songwriters with No. 1 hits, he was the lead singer for a Swedish band in the ’80s that was trying to be Bon Jovi, and they never caught on. His band was called It’s Alive. You can look their songs up online. They’re not that great, but he wound up making all these incredible records with all these different people. 

There’s a lot of that. That has happened many, many times throughout pop history. It’s certainly one way to deal with the flop problem.

Until recently, Natalie Harp was an omnipresent but low-profile aide to President Donald Trump: always there, but rarely part of the story herself. That changed abruptly earlier this month, when Sen. Jon Ossoff (D-GA), who is currently running for reelection, name-dropped her in a speech. 

Trump “doesn’t want to do the job. He wants to build his ballroom and travel with Natalie on their apparently defenseless flying palace gifted by the Emir of Qatar,” Ossoff told supporters at a rally.

The line was a reference to reporting on Trump’s catering-cart maneuver as he was flying back from Turkey in July; Harp and other Trump aides joined the president on an alternate plane by way of a catering cart, while Secretary of State Marco Rubio was left behind on Air Force One. 

The “Natalie” jab from Ossoff quickly took on a life of its own, spurred by a furious response from the Trump White House and right-wing media. Somewhat lost in the flurry of attention on Harp was Ossoff himself — but Greg Bluestein, chief political reporter for the Atlanta Journal-Constitution and co-host of the Politically Georgia podcast, told Today, Explained that the remark was “by design.”

Bluestein spoke with Today, Explained co-host Sean Rameswaram about Ossoff’s disciplined, savvy messaging strategy, his political rise, and why his rhetorical jabs at Trump are fueling speculation about an Ossoff 2028 presidential run.

Below is an excerpt of their conversation, edited for length and clarity. There’s much more in the full podcast, so listen to Today, Explained wherever you get podcasts, including Apple Podcasts, Pandora, and Spotify.

It’s time on this show, Greg, that we remind people who Jon Ossoff is. I’m told that is a job with which you can help.

I go way back with Sen. Ossoff. The first time I met him, or at least I talked to him, was way back in early 2017 where I got a call out of the blue from a name, a number I didn’t recognize, and the voice on the line said, “Hi, I’m Jon Ossoff and I’m running for US House, this special election.” And I said, “Well, welcome to the show. There’s about 17 other candidates already in the race.” 

And he goes, “Well, I’ve got something they don’t. I have John Lewis’s endorsement, and I have about $250,000 in cash commitments.” So I was like, “Okay.” 

It still was an uphill battle because we’re talking about a deep red Republican seat in the northern suburbs of Atlanta at a time when all those suburban seats were still Republican. So I said, “Okay, good luck, sir.”

But lo and behold, he became a national figure in that loss. 

So you’ve been covering Sen. Ossoff just about as long as anybody. At any point over the course of that almost-decade, did you expect “Natalie” from him? 

No. I mean, look, you expect him to be really, really careful and calculated about what he says. Even back then, he rarely uttered an imprecise statement. There have been times where folks have caught him off-message, but it’s been very, very rare even at the beginning of his political career, certainly now. 

When he uttered the “Natalie” line that sparked a thousand thought pieces and national takes and all that, that was done by design. 

Tell us a bit about his backstory for people who have forgotten who Jon Ossoff is.

When I first got that call in early 2017, I had no idea who he was. Little did I know he’d become a national figure that we’d be talking about in the context of a presidential campaign not even a decade later. 

He’s a former documentarian, a former intern of the legendary Georgia Congressman John Lewis, whose parents, especially his mom, were involved in Democratic politics in Georgia, but definitely not household names — definitely not a known quantity when he called me all those years ago to say “I’m running.” 

Ossoff came within a whisker of an outright win, which would’ve been a huge, monumental upset. But in the process, he showed that Democrats have a path with suburban voters that long voted Republican in the Trump era. He started with the sort of campaign slogan of “Make Trump Furious.”

He was leaning into the Democratic activism, but then within weeks shifted his message toward a more friendly, more mainstream argument about bringing jobs to the district, bringing more tech-savvy investment to the district. 

When he announced for US Senate against David Perdue, very few people gave him a shot when he got in the race. But that race ended with this epic double-header runoff because Rev. Raphael Warnock was also in the race against [Sen.] Kelly Loeffler. Democrats hadn’t won in Georgia in decades. So it was an epic election and a real nail-biter to the end. 

Ossoff becomes the first Jewish US senator in Georgia history, Warnock becomes the first Black US senator in Georgia history, and together they flip control of the Senate and allow Joe Biden to to actually implement some of his broad-ranging agenda those first two years that they were in office.

It makes a lot of noise when Ossoff helps flip the US Senate along with Warnock. And he’s making a lot of noise now with “Natalie.” But I can’t say that I feel like he’s made a lot of noise in the intervening six years. What’s he been like as a senator?

That’s by design. It’s only been really recently where he’s been very willing to go on the national cable shows, to talk to national reporters more, to do a lot of the things that you see other nationally prominent Democratic figures do much more regularly. 

We both know there are folks in Washington who love going to the White House Correspondents’ Dinner and they love going to this or that luncheon or this or that dinner. Sen. Ossoff is much more likely to quietly go home and spend time with his two kids. 

I’m not just saying that because that’s the senator I know. He is much more reserved and guarded about his private life and will bend over backwards to figure out ways to get back to Georgia — even when there are important votes, [he’ll] find ways after those votes to get back for events with his kids and that kind of thing.

It feels a little contrary to think about this guy who keeps a low profile, who wants to go back home to Georgia to be with his family, who doesn’t want the limelight, because as you’ve already mentioned, he isn’t just running for reelection in the Senate right now. Everyone seems to believe that he’s running for president.

I’m going to go out on a limb saying that I believe him when he said publicly — and privately too — to folks all over the spectrum, media folks and activists and supporters and you name it, that he is focused on this election and he’s not running for president.

If someone like Sen. Ossoff wins by a huge margin over Mike Collins in an important battleground state that is tilted both ways the last decade, the chatter will not stop. It’ll only get louder. 

[He is] someone who is adept at making the arguments that so many core Democratic voters want to hear about President Trump, but at the same time can win over swing voters like he has in 2021. And he’s already seeming like he’s certainly making that outreach to them in 2026.

Do you think that if he does end up there, we’ll look back at Nataliegate as a big moment for him where it was just clear that this guy had the stuff? Or does this feel like, a week and a half out or whatever it is now, that it’s already fading into the background?

The biggest takeaway from that to me was how — and I think Jonathan Martin from Politico was the first to say it — Ossoff was essentially the nation’s assignment editor because it spurred countless stories for the next week and a half about who Natalie Harp is. 

It was Ossoff who showed that he has this extraordinary staying power in the media. These rallies — he doesn’t hold them every day or every week. These are like once every month or so rallies.

The stagecraft is impressive. He’s got these multi-camera shots that are immediately farmed out to all these social media accounts who amplify them. It’s very, very impressive how he pulls this off. And they’ve become these sort of national spectacles that have inevitably given rise to more ruminations about whether he’ll run for president or not, but also of course boost his campaign itself. 

That to me was one of the takeaways — that he has this impressive grip on not only what the media’s covering, but triggering them to cover even more of it.