On July 2, 1988, Michael Jackson’s “Dirty Diana” reached the top spot of the Billboard Hot 100, creating chart history in the process. The No. 1 hit was the fifth straight off Jackson’s 1987 album Badbreaking a tie with the Bee Gees-led Saturday Night Fever soundtrack from 1977 and Whitney Houston’s own ’87 album Whitney – making the global superstar the first artist with five Hot 100-topping singles on the same LP.

Over the next few years, the record was approached several times. George Michael’s Faith came one spot away, scoring a No. 2 hit and then four No. 1s, but failing to land that historic fifth chart-topper. Paula Abdul’s Forever Your Girl notched four No. 1s, after which Abdul would not release another single until she’d already moved on to her next album. Janet Jackson’s Rhythm Nation 1814 set a Hot 100 record with seven top five hits, but again, only four No. 1s. And finally, decades later — after the 1991 introduction of SoundScan and BDSRadio technology (now MRC Data) to Billboard’s chart methodology made for more accurate tracking, resulting in longer average runs at No. 1 and, thus, fewer No. 1-stacked blockbuster LPs — Usher’s Confessions made a run in 2004, also getting to four Hot 100-toppers and tapping out just short of the fifth.

It wasn’t until 10 years ago this week in 2011 that an album would finally tie Michael Jackson’s hallowed Hot 100 record for No. 1 singles off an album. And the set that did it was one of the defining LPs from a new golden age in mega-pop: Katy Perry’s Teenage Dream.

It’s safe to say that Teenage Dream was a less-probable candidate for five Hot 100-toppers than Bad had been 23 years earlier. Jackson was already the unquestioned King of Pop by the time of Bad, having made myriad other forms of chart history a half-decade earlier with his industry-shifting Thriller, but Perry just had one charted album (and one Hot 100 No. 1 hit) to her credit. Stomping breakout single “I Kissed a Girl” had taken her to the top spot in July 2008, and subsequent top 10 hits “Hot n Cold” and “Waking Up in Vegas” — all off 2008’s One of the Boys, her first full LP since rebranding from Katy Hudson — proved it wasn’t a fluke. But her continued dominance was no guarantee, especially entering into an era that would prove among the most loaded for female pop stars in top 40 history: Lady Gaga, Beyoncé, Rihanna, Kesha, Britney Spears, P!nk, Nicki Minaj, Taylor Swift, Kelly Clarkson and soon enough, Adele.

But Perry, by then established as a star in her own right, saw an opportunity to step things up on her second album, both commercially and artistically. “She’d had some really big success, but she was nowhere near comfortable riding on that,” Greg Thompson, then-evp of promotion and marketing at Perry’s Capitol label says. “Katy clearly saw that she had the ability to do more. She saw the ability to make an even better record, and I think a record that she could have her fingerprints all over every single track.” Her drive at the time was particularly relentless. “I might have made her fly from Japan to Charlotte, North Carolina, to do a Halloween show on her birthday,” Thompson says, chuckling. “[There was] none of this, ‘Well it’s my birthday, I don’t really wanna do that…’ It was like, ‘No, this is what we need to do.’”

Perry and her team also took note of the evolving musical landscape around them — which, thanks to the rising impact of dance music and the always-expanding influence of hip-hop, had moved top 40 away from the rock-based pop music that had defined the pop star’s first mainstream go-round. “As we got into 2009, the marketplace started shifting a bit more rhythmic,” says Chris Anokute, the then-senior A&R director at Capitol, who originally helped bring Perry to the label. “So we set out to kind of compete and stay relevant, and make music that was obviously forward-sounding — still maintaining her pop/rock, band essence, but taking it a bit further and making rhythmic records, records that Katy wasn’t making it in the past.” 

The first advance single released from Teenage Dream, 2010’s “California Gurls,” would certainly take it that bit further. It was just as propulsive as “I Kissed a Girl,” but with a lighter, frothier, and more electronic touch than that previous lead single’s bulldozing pop-rock. “Gurls,” recorded with the superproducer team of Max Martin, Dr. Luke, and Benny Blanco, was an unapologetically bubblegum fantasia — albeit with just enough PG-13 edge to keep it out of Radio Disney territory — packing a ’90s throwback vibe, an Adult Candyland-set music video and a knockout chorus that invoked the Beach Boys and G-funk in equal measure. Inspired in part by the success that native New Yorkers Jay-Z and Alicia Keys had the year before big-upping the Big Apple, Perry’s ode set to do the same for her own home state.

“She came in and was like, ‘You know, “Empire State of Mind” is so big… like, what about the West Coast?’” co-writer Bonnie McKee — a longtime friend of Perry’s, collaborating with her for the first time on the Teenage Dream sessions — recalls the star brainstorming. “Like, ‘We need to represent.’ And that’s what we did!”

But the real coup of “California Gurls” was securing a guest verse from one of the state’s preeminent musical icons, Snoop Dogg. Anokute remembers texting with Snoop while on a date with his girlfriend (now wife), trying to persuade him to come listen to the track — and then having to leave her with friends when the rapper decided to pop by the studio. “I’m like, ‘Babe, Snoop is literally coming to the studio to meet Katy and Max and Luke, and he’s gonna hear ‘California Gurls’ — I gotta go,” he recalls.

The team was giddy to have Snoop in the building, and he quickly connected with the song’s vibe. “I remember him rolling up a blunt, he listened to the record a few times, he went in the booth and he cut the record — he knocked it out right away,” Anokute says. “We were all just high-fiving in the studio, like, ‘YAY!

While the song was among the last to come together for Teenage Dream — McKee remembers thinking the album was done, prior to Perry’s Cali epiphany — it was quickly tabbed as the set’s lead single. The timing was ideal, with the warm-weather months approaching. “California Gurls” was the perfect summer record,” Thompson says. “Y’know, Snoop, bikinis on top, Daisy Dukes — those lyrics scream ‘summer,’ right?”

To hedge their bets, he and Perry trekked around the country to host seasonal parties for radio and retail gatekeepers. “We brought in trucks full of sand, and eight-foot round beach balls, and we would sit everyone down, get a cocktail, have a lot of fun,” Thompson says. “And I would be the dumb, stupid record guy, and she’d be the beautiful pop star, and we would start to introduce tracks.” 

“California Gurls” was a runaway success at both radio and iTunes, selling 294,000 digital downloads in its first week and debuting at No. 2 on the Hot 100 — reaching the top spot three weeks later, on the chart dated June 19, where it would stay for six total weeks. But while the song’s success was massive and immediate, the feedback Perry and Thompson received for multiple tracks played at their gatekeeper parties encouraged them that it would be far from unmatchable. “Every night, the most jaded guys walked out of that room going, ‘Man, I just heard four, five, six hit records,’” Thompson says. 

Next up would be the set’s title track, a dreamier, more rock-based cut, again co-helmed with Luke, Martin and Blanco and co-penned by McKee. With its melody already set, the writer had gone through “seven different lyrics, all the way through,” she says, before she was able to crack the code on it. “I went and had my 8 Mile moment when I was like, ‘This is your chance!’” remembers McKee, who was at a career low-end prior to coming to Santa Barbara to work on Perry’s album. “I was just thinking about my first kiss, and what it was like for me in middle school or whatever, and dreaming about my first boyfriend and what that would be like… and ‘Teenage’ came into my head. And I thought, ‘That says a lot. That packs a punch.’” 

With its young-love concept in place, the song took flight, quickly turning into one of the most soaring pop-rock singalongs of the early decade, keyed around a punch-the-air chorus as anthemic as anything Jon Bon Jovi ever wrote. Anokute remembers being particularly effusive about his praise for the finished song upon hearing it for the first time: “When I heard that record, I was like, ‘This may be the greatest song ever written.’ Because it was just so colorful. It reminded me of my childhood. It just felt like hope. It felt nostalgic. And it was shiny, and it was the guitars, and that chorus…” 

The single was released in late July, along with a gauzy, nostalgic and summery music video, with Thompson — who had already sketched the album’s entire rollout in seasonal terms — viewing it as “the perfect back-to-school record… every kid could relate to that record.” The song’s velocity was only slightly slower upon debuting than “Gurls,” bowing at No. 20 and then taking seven weeks to climb to No. 1, where it stayed for two weeks. By that point, the Teenage Dream album had also been released, dropping on Aug. 24 and topping the Billboard 200 albums chart (dated Sept. 11) with 192,000 copies sold in its first week.

Thompson remembers getting some flak for the album’s first-week number — which was fairly strong for the period, after a decade-plus of file-sharing had significantly depressed the album sales market, but was still well short of the totals being moved by stars like Taylor Swift and Beyoncé at the time. “I think that people started to raise the bar way too high, and not take a longview perspective,” he says. “I was more focused on, ‘How many No. 1 records can we get off this album?’”

With two No. 1s down already, Teenage Dream would go for a third that October with the release of “Firework.” Swapping out the Luke-Martin-Blanco team for Norwegian producer duo Stargate — and their regular collaborator Ester Dean for Bonnie McKee as co-writer — Anokute had booked the session for Perry on a short trip to New York that was taking, forcing her to bond quickly with her new collaborators. “They wrote that song the first day,” the A&R director says. “And the vocal you hear on “Firework,” for the most part, is the vocal that she cut when she wrote the song with Ester Dean.”

The pulsing single was a departure for both Perry and for Stargate, who had risen to prominence in the second half of the ’00s cutting acoustic-based, mid-tempo R&B crossover singles with Rihanna, Ne-Yo and Beyoncé. But with “Firework” and Rihanna’s “Only Girl [In the World]” in 2010, the producer duo embraced the rise of dance-pop and EDM, and their newly high-BPM hits fit right alongside party-starting singles from the likes of David Guetta and The Black Eyed Peas. “Firework” also explored new lyrical territory for Perry, who harnessed the song’s glowing energy for her most motivational, affirming single to that point. Anokute recalls the singer telling him upon hearing the song for the first time that she knew the song would transcend its moment: “Katy’s like, ‘This is my evergreen. This is the song that will always give.’”

“Firework” also came equipped with the third memorable music video of the Teenage Dream run. Shot in Budapest at night, the clip was a far cry from the summer madness of the album’s first two visuals — instead showcasing some of the outsiders sung to in the song’s lyrics taking control of their lives, and (along with Perry) shooting the titular explosives out of their chests. “We treated every single like a marketing plan for a new album — and every track had a plan, every video had a massive ambition,” Thompson says. “We made those videos so that every video was like a new Katy Perry movie.” 

After a more modest No. 57 debut, “Firework” also shot up the Hot 100, becoming Teenage Dream’s third straight No. 1 single on Dec. 18 — making good on Thompson’s hope to “crush ‘em at Christmas” with the song — and holding on top for four non-consecutive weeks. (The next August, “Firework” would also win video of the year at the 2011 MTV Video Music Awards.)

Despite the smooth sailing the set’s first three singles had on their way to the Hot 100’s peak, by single No. 4, Perry & Co. knew they were gonna need a little extra help. The (literally) out-of-this-world love song “E.T.,” tabbed as the next song up for February 2011, was another new sound for the pop star — built around a slamming production that co-producer Ammo had started while cooking up beats for Three 6 Mafia — and the team decided they needed a remix for the single version. “By doing it, you freshen up the song for an album now that had been out for six months,” Thompson explains. “You also sort of gave the song more dimension, and made it even much more attractive to radio by putting two of the hottest artists in the world together on one song.”

That other super-hot artist added to the song’s new single edit was Kanye West —  also published by Capitol’s then-parent group, EMI — who was fresh off the most acclaimed album of his career, My Beautiful Dark Twisted Fantasy. Anokute cites Dan McCarroll, then Capitol’s president, as having the idea to get Kanye on the record, and Jon Platt, EMI’s vice president, as the guy who got it done, leading to West adding a pair of punny verses to go over the song’s intro and after its bridge. (“It was expensive to get [Kanye],” says Thompson, who also remembers the song’s outer space-set video costing a pretty penny: “The overages were so bad, I said, ‘Are you guys out there making Waterworld?’”)

The costs proved worth it, as “E.T.” re-entered the Hot 100 at No. 28 in March — after a brief appearance the previous year as a Kanye-less promo single — and topped the chart just five weeks later (dated April 9) for the first of its five nonconsecutive weeks on top, making it four-for-four for Teenage Dream. At that point, the records that Perry and her team were approaching became unignorable. “After ‘E.T.,’ I think everyone started to realize that we were doing some historic stuff here,” Thompson says. “So we’re clearly looking it at, going, ‘Hey, we gotta pull out all the stops… Anybody that’s got an idea, bring it to marketing. Let’s figure it out.”

The fifth song Perry elected to try to seal the deal with was “Last Friday Night (T.G.I.F.),” another Luke/Martin co-production, with McKee back in tow as co-writer. The boisterous pop-rocker, told from the perspective of a confused morning after and released in June of 2011, was a return to the sunny party vibes of the album’s first two singles, and took many real-life details from Perry’s and McKee’s wilder early 20s together. “We loved to party back in the day, and there were a lot of backyard barbecues and hungover mornings,” McKee says. “So that one was pretty easy to write, because we had a lot of experience with that!”

And as Thompson proclaimed they would, Perry and her team pulled out all the stops. Katy revealed new social media profiles for a nerdy alternate identity (under the name Kathy Beth Terry) in order to build hype for the song’s ’80s-themed video — which would premiere a week later with cameos from period hitmakers Kenny G and Debbie Gibson, as well as ’90s brother band phenoms Hanson, Glee stars Kevin McHale and Darren Criss, and another recent “Friday” sensation, viral teen singer Rebecca Black. It was enough to help propel the song, which re-entered as a single at No. 63 in June 2011, to No. 2 on the Hot 100 — where it got stuck for three weeks behind LMFAO’s “Party Rock Anthem.” It seemed the song would need an extra boost to put it over the top. “We need to go deeper on this one,’” Thompson remembers telling the team. ‘This is the fifth single, guys. I’ll take a remix, I’ll take a feature.’”

Thompson got his remix and feature, with a new version of “Last Friday Night” featuring rap legend Missy Elliott arriving right in the nick of time. “iTunes had exploded, and we knew that if we dropped a remix, Katy fans would want to have both [versions] — so it would boost her consumption,” he says. The remix wasn’t as seamless a fit as Kanye’s “E.T.” verse, but it drove just enough extra interest and sales towards the song to get it over the hump. On the Hot 100 chart dated Aug. 27, 2011, “Last Friday Night” finally climbed to the top spot — staying there for two weeks — making it five No. 1s for Teenage Dream, and tying Bad for the all-time record. “I’m sure that the night that went out [to celebrate], we put a serious debt in my expense account,” Thompson says. 

But Teenage Dream wasn’t done yet. “The One That Got Away,” a mid-tempo paean to lost love, was released in September as the album’s sixth single, with its sights now on breaking Jackson’s record. With an action-packed music video (and a teaser narrated by Rock and Roll Hall of Famer Stevie Nicks), performances of the song on The X Factor and the American Music Awards, and eventually an acoustic version released to digital retailers, the team certainly gave “The One” another full push, and were able to get it as high as No. 3 on the Hot 100 in January 2012. But this time, not even a late-arriving remix — featuring pop-friendly rapper B.o.B. — could push the single to the top spot. (“That was a little bit of a heartbreak,” admits Thompson.)

There could have been singles still to pull from Teenage Dream — fan favorites like the burstingly joyous “Hummingbird Heartbeat” or the melancholy “Not Like the Movies” — but after “The One,” the team turned their attention to a reissue of Teenage Dream, entitled The Complete Confection and boasting three entirely new songs. One of those, the breakup banger “Part of Me,” was actually the first song that McKee helped write as part of the Teenage Dream era, and it debuted at No. 1 on the Hot 100 in March. (“Wide Awake,” the follow-up single off Confection, peaked at No. 2.)

Perry’s team sees it as something an asterisk on the record they technically still share with MJ. “I was kinda bummed,” Anokute says. “Because I knew that if there wasn’t a repackage — and all those songs, including ‘Part of Me’ and ‘Wide Awake,’ were on the main album — she would’ve basically broken Michael Jackson’s record.”

But in the 10 years since Teenage Dream made history, no other album has threatened its mark of five Hot 100 No. 1s. Of all the other biggest blockbuster albums of the 2010s and ’20s — Adele’s 21, Taylor Swift’s 1989, Rihanna’s Loud, Justin Bieber’s Purpose, Drake’s Scorpion, right up to The Weeknd’s After Hours — none have spawned more than three No. 1s, as the streaming age has made promoting individual songs off an already-released album a much trickier proposition than it once was. “I just think the business changed,” Anokute says. “Everything is streaming-driven. If you’re not streaming, you’re not getting on the radio, and if you’re on the radio, it doesn’t mean you’re penetrating pop culture…  radio used to drive the marketplace, and I think Katy Perry’s the Last of the Mohicans. I don’t know if you’ll ever have another artist — I don’t know if it’s possible to have another artist have five No. 1s on one album.” 

Ten years later, Perry’s team looks back on the Teenage Dream era as one of the defining experiences of their professional lives. Anokute, who still considers Perry a “dear friend,” and even A&R’d her Smile album in 2020 despite leaving Capitol for Universal midway through the Teenage Dream era, considers it “the greatest work project of my career.” McKee, who was struggling to pay her cell phone and utility bills before getting the call to work on Teenage Dream, fondly remembers the validation of being put up at the Four Seasons while working on the LP in Santa Barbara, convinced something big was going to happen with all of it. “I drew a hot bath and got in and just sobbed tears of joy — like, ‘I’M GONNA BE OKAY!’” she says. “So I’m incredibly grateful to Katy and the whole team for including me.”

And Thompson, who says he was an “obsessive nerd” when it came to the Hot 100 in those days, calls the five No. 1s off Teenage Dream “100% my favorite” chart achievement. “To achieve these kind of records… it’s just a blessing to be part of that. And I’ve been fortunate to work with a lot of big artists and a lot of different things in my career, and I knock on wood and appreciate that every day. But to be with Katy on that journey was the most amazing thing in my career.”

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