Katy Perry’s 20 Biggest Hits

Released: August 3, 2010
Chart Peak: Number 53

Perry hasn't always had the best chart success with ballads. This promo single, its lyric disillusioned yet still willfully naïve, is notable mostly for spanning two stages of Perry's life: She started writing it just before meeting Russell Brand, and finished it after the two became a couple.

Released: August 12, 2013
Chart Peak: Number 48

It's eerie to hear both halves of a now-defunct celebrity couple confess that they fell for each other despite their better judgment. Mayer brings out a quieter side of Perry, who turns in one of her most understated vocal performances.

Released: January 18, 2010
Chart Peak: Number 37

By his own account, tim.he.is heard the Black Eyed Peas and decided to record his own "I Gotta Feeling," with Katy apparently as his Fergie. It gently brushed the lower reaches of the Top 40.

Released: September 30, 2013
Chart Peak: Number 34

With its deep house beat and hammering pianos lifted from turn-of-the-Nineties Eurodance, this is Perry's most straight up (and most retro) dance single. It lost out to "Dark Horse" in a Pepsi-sponsored contest to determine the next single from Prism, but was released to iTunes anyway and – naturally – charted nonetheless.

Released: January 12, 2009
Chart Peak: Number 29

In the days of Perry's breakthrough LP, One of the Boys, it was uncertain as to which direction she would go. "I Kissed a Girl" had a Gary Glitter whomp that she showcased to rock fans on the 2008 Warped Tour, and "Thinking of You" could have soundtracked a WB teen show in 2001. Despite being two early hits, both those potential directions turned out to be fake outs.

Released: April 21, 2014
Chart Peak: Number 17

Perry is as unsubtle on this disco homage as the Saturday Night Live horn section that drives the tune home. Just in case you think she doesn't mean what you think she means when she threatens "to break out the big balloons," she follows up with a mention of "your birthday suit."

Released: October 16, 2013
Chart Peak: Number 14

The Prism single released between "Roar" and "Dark Horse" didn't perform as well as its chart-topping bookends, but still topped Hot Dance Club Songs in the first week of 2014.

Released: April 7, 2009
Chart Peak: Number Nine

Perry claims this is based on a fake marriage she and a pal arranged as a stunt to freak out their friends and family. It's her one collaboration to date with storied song doctor Desmond Child, the man behind "Livin' on a Prayer," the man who revived the careers of Aerosmith and Cher in the Eighties, the man who will be writing Bonnie Tyler album tracks until who-knows-when.

Released: October 4, 2011
Chart Peak: Number Three

Or "The World Record That Got Away." Five singles from Teenage Dream went to number one – the only other album that had produced so many chart toppers was Michael Jackson's Bad. But, sadly, this was not to be the sixth – maybe not as many people make out to Radiohead as Katy thinks?

Released: September 29, 2008
Chart Peak: Number Three

Not many pop stars can claim to have been slut-shamed by Sesame Street. But though Perry's far-from-G-rated original was adapted to an age-appropriate lesson for Elmo about antonyms, her appearance was cancelled: She was sponsored by the letter 2 for "too much" and the letter C for "cleavage."

Released: May 22, 2012
Chart Peak: Number Two

Here's where it gets personal. Written after her divorce from Russell Brand, this is the first Perry hit that demands awareness and interest in her autobiography, and it elevated her to a new level of stardom. It's the first day of the rest of Katy's life – or at least her career.

Released: February 13, 2012
Chart Peak: Number One (One week)

After the Brand-Perry's divorce, this leftover from the original Teenage Dream sessions was neatly retrofitted to illustrate the maturity Perry had achieved through overcoming adversity. And that insistent house beat takes on an unmistakable military feel when you watch the video of a heartbroken Katy determined to Private Benjamin her way through Marine boot camp.

Released: June 6, 2011
Chart Peak: Number One (Two weeks)

The tune's a straight-up teen fantasy of naughty rule-breaking fun, and the video's an age-appropriate fit, with "Kathy Beth Terry" receiving a makeover and achieving popularity and featuring cameos from teen stars of various eras, including Rebecca Black, Corey Feldman, Hanson and Debbie Gibson. Oh, and also Kenny G – even he must have been a teen once, right?

Released: July 23, 2010
Chart Peak: Number One (Two weeks)

According to Perry's songwriting partner Bonnie McKee, this shimmering fantasy of self-conscious naïveté went through several conceptual reworkings before it met the approval of her production team. At various stages, it was an unsexy Peter Pan homage, a jokey tune about growing up to be a "mom in a minivan" and an extended clothing metaphor about sex.

Released: August 10, 2013
Chart Peak: Number One (Two weeks)

This spunky anthem stomped up the charts leaving a flurry of silly controversies in its wake. First Perry was accused of jacking the tune of Sara Bareilles' "Brave" (though not by Bareilles herself). Then moombahton producer Dillon Francis claimed she stole the concept of an emoticon-centered video from him. Finally, fans of the Cincinnati Bengals were outraged to hear their team play such an unmacho track during the player introductions.

Released: October 18, 2011
Chart Peak: Number One (Four weeks)

Has there ever been a better year to have low self-esteem than 2011? From Gaga's "Born This Way" to Pink's "Fuckin' Perfect," pop music was so relentlessly inspirational that over-empowered people across America were running out of goals to achieve. Fortunately, there were still a few million plastic bags and houses of cards left for Perry to pep talk even this late in the year.

Released: December 17, 2013
Chart Peak: Number One (Four weeks)

Beware Katy's awesome power to overhaul the English language. This time last year, a "dark horse" was just an underdog. One smash hit later, that phrase instead conjures a malevolent witchy seductress that not even Juicy J can hit and quit. Dr. Luke's modification of trap music elements is no less drastic.

Released: February 16, 2011
Chart Peak: Number One (Five weeks)

Well before he signed Juicy J to his Kemosabe label, Dr. Luke was working up a beat for Three 6 Mafia that Katy appropriated for her own moody hit. And maybe you've heard of the special guest on the remix?

Released: May 7, 2010
Chart Peak: Number One (Six weeks)

This was written as a frothy Pacific counterpoint to "Empire State of Mind," and you can hear the video's pastel artificiality in its production. What an ideal visual and aural setting for a charismatic Cali space cadet –we mean Snoop Dogg, whose appreciative leer is way more David Lee Roth than Brian Wilson. If the title reminds you Big Star's "September Gurls," Perry's manager Bradford Cobb suggested the spelling as a tribute to Alex Chilton, who had passed earlier that year.

Released: April 28, 2008
Chart Peak: Number One (Seven weeks)

Perry has strewn contradictory autobiographical half-truths about which girl she did or didn't kiss on her first (and biggest) hit with a faux candor that's downright Dylanesque. Maybe a high school bestie really was her experimental game, maybe she was just fantasizing out loud about tasting ScarJo's cherry chapstick, maybe she made the whole thing up – songwriters do that sometimes, you know.