Miey Cyrus and Taylor Swift, 2009.
 Kevin Mazur/WireImage

Pop isn’t necessarily a young person’s game. Singing, rapping, songwriting, melting minds with various instruments: These are skills that improve with time, and plenty of veteran artists produce music that resonates with fans of all ages -- even fickle teens that are generally suspicious of adults. That’s what makes the artists behind these 21 songs so remarkable. They all bumrushed the charts before reaching legal drinking age, and in many cases, the hits they scored as teenagers remain their signature tracks.

In celebration of our 2014 21 Under 21 list, we've combed the Billboard charts to come up with this list of the 21 biggest hits from the past 21 years that were recorded by artists who were under 21 at the time of the song's release. They’re inspirations for young dreamers everywhere and proof that a lack of experience doesn’t prevent one from grabbing the world by the ears.

This chart is based on actual performance on the weekly Billboard Hot 100* from Sept. 24, 1993 to Sept. 24 2014. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least. 

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21. Miley Cyrus, “Wrecking Ball”
Hot 100 Peak Position: 1, Peak Date: September 28, 2013

When you’re young and in love, it’s easy to feel like a giant steel ball swinging around at dangerous speeds. That must have been especially true for 20-year-old Miley, who split with fiancé Liam Hemsworth just weeks after this song was released. She didn’t write the tune, but as she toured the world, singing lines like “All I wanted was to break your walls / All you ever did was wreck me,” her words hit like sledgehammers, heavy and true.

20. Monica, “Angel of Mine”
Hot 100 Peak Position: 1, Peak Date: February 13, 1999

The third single from Monica’s breakout The Boy Is Mine album is certainly the sweetest. By the time this dropped, the 18-year-old Atlantan had tussled with Brandy on the disc’s title track and chosen to delay sex on the follow-up single. Here, she thanks a boy—almost certainly not the same one mentioned on either of the aforementioned tracks—for showing her the meaning of love.

19. Avril Lavigne, “Complicated”
Hot 100 Peak Position: 2, Peak Date: August 3, 2002

“Life’s like this,” Avril says at the outset, like she’s got it all figured out. Really, though, the 18-year-old Canadian was as confused as anyone, and this song is all about trying to make sense of poseurs who are punky one minute and preppy the next. Not that “acting like you’re somebody else” is really a crime. Whether you’re a teenager or a pop star, it’s kind of expected.

18. Christina Aguilera, “Genie In a Bottle”
Hot 100 Peak Position: 1, Peak Date: July 31, 1999

Just like Britney Spears didn’t really want to be “hit,” her chief ’99 teen-pop rival wasn’t looking to be rubbed, physically speaking. The 18-year-old’s heart is triumphing over her body, and here, she tells a guy that he’s got to treat her right and respect her before he can expect any loving. There’s the rub.

17. Taylor Swift, “Love Story”
Hot 100 Peak Position: 4, Peak Date: January 17, 2009

This is why high schoolers shouldn’t read Shakespeare. They get these grand ideas about love, and here, 16-year-old Swift gets so swept up in the romance of the Bard’s words that she imagines a new ending for Romeo and Juliet—one in which the two avoid the whole double-suicide thing and get hitched. Whether that’s really the “happy ending” depends on your opinion of marriage.

16. Jason Derulo, “Whatcha Say”
Hot 100 Peak Position: 1, Peak Date: November 14, 2009

Derulo was just shy of 20 when he released this not-quite-apologetic R&B number, and his youth might account for the wrongheaded way he tries to make amends for screwing around. “Cause when the roof caved in and the truth came out / I just didn't know what to do,” he tells his lady, “But when I become a star we'll be living so large / I'll do anything for you.” Best case: Newly rich JD goes from cheating on his missus to cheating on his taxes.

15. Rihanna, “Disturbia”
Hot 100 Peak Position: 1, Peak Date: August 23, 2008

On this dark banger, written by Chris Brown and his team, Rihanna suffers a “disease of the mind” that can “consume you” and make you “feel like a monster.” It’s goth-flavored bubblegum sprinkled with complex emotions that were hardly unique to Rihanna. “I gotta get out or figure this shit out,” she sings, speaking for herself and just about every other 20-year-old on the planet.

14. Ciara featuring Missy Elliott, “1, 2, Step”
Hot 100 Peak Position: 2, Peak Date: January 8, 2005

The early-‘80s electro-funk jams that inspired this badass Jazze Pha production dropped before Ciara was born, but the beat is “outrageous” and “so contagious,” so historical context isn’t really a prereq. Neither is the ability to count beyond two, which is fortunate, since America lags behind much of the world in math skills. Props to 18-year-old Ciara—who co-wrote the tune with Pha—for going easy on everyone.

13. Rihanna featuring Jay-Z, “Umbrella”
Hot 100 Peak Position: 1, Peak Date: June 9, 2007

For as much as grief as Ri gets for living dangerously, she’s obviously got a sensible streak. Even at 19, she never left the house (or champagne-bottle-strewn hotel suite) without reading the weather and, when necessary, grabbing an umbrella. She’ll even let your non-forecast-checking ass stand under it.

12. Taylor Swift, “You Belong With Me”
Hot 100 Peak Position: 2, Peak Date: August 22, 2009

It’s usually the dorky boy doing the pining, so credit 19-year-old Taylor Swift with flipping the script and going sexy She-Urkel on this country-pop mash note from the girl next door. She gets extra credit for singing that part about “standing by and waiting at your backdoor” and not sounding like a total stalker.

11. Monica, “The First Night”
Hot 100 Peak Position: 1, Peak Date: October 3, 1998

Parents and sex-ed teachers must have loved this one. “I wanna get down,” Monica sings, “but not on the first night.” Whether this 18-year-old was singing about saving herself for marriage or just the second date, it’s a song that makes caution sound sexy.

10. Chris Brown, “Run It!”
Hot 100 Peak Position: 1, Peak Date: November 26, 2005

“I can definitely show you things that’s go’n have you sayin’ I can’t be 16,” Breezy promises on this synth-powered club jam. Now, there’s something aggressive and underhanded about his come-ons—“Is your man on the flo’? / If he ain’t, let me know”—but it’s unfair to read too much into this song. At this point, Brown was just a cocksure teen bugging out over a girl in tight jeans. There’s nothing unusual here but his talent.

9. Ciara featuring Petey Pablo, “Goodies”
Hot 100 Peak Position: 1, Peak Date: September 11, 2004

Who says women don’t know what they want? “Baby, this is what I’m looking for: sexy, independent, down-to-spend-it type that’s getting his dough,” Ciara sings 40 seconds into this smash, which she co-wrote at the age of 19. Once she’s described her ideal suitor, Ciara spends the rest of the song telling broke-ass pretenders why they’ll never get in her cookie jar. Petey Pablo acts unimpressed, but this ain’t one of his “bada boom, bada bam-ba-bam” girls.

8. Alicia Keys, “Fallin'”
Hot 100 Peak Position: 1, Peak Date: August 18, 2001

In romance, the planet’s physical laws get all screwed up. You can fall in and out (and back in and back out) of this crazy state called love. Although Keys attended New York City’s Professional Performing Arts School, where they don’t produce a ton of physicists, she picked up that bit of what you might call emotional science—the crux of the then-20-year-old’s stunning debut single.

7. Soulja Boy Tell'em, “Crank That (Soulja Boy)”
Hot 100 Peak Position: 1, Peak Date: September 15, 2007

Beneath all the self-assurance, 17-year-old Soulja Boy might have been as insecure as most others his age. This song’s hook—“Soulja Boy up in this ho / watch me crank it, watch me roll”—reads like a personal mantra, the type Hindu wise men have been promoting for millennia. Some mantras are pure gibberish that nevertheless provide spiritual power—just like this song.

6. Destiny's Child, “Independent Women Part 1”
Hot 100 Peak Position: 1, Peak Date: Novermber 18, 2000

Every teenager dreams of moving out of mom and dad’s place, and here, 19-year-old Beyonce and her gals paint the ultimate portrait of independence. “The shoes on my feet / I’ve bought it,” the ladies sing, their vaguely taunting tone aimed at anyone who’d dare keep a strong young woman down. “The clothes I’m wearing, I’ve bought it.” Even if you’re shopping at DSW and Marshalls, it’s damn nice being beholden to no one.

5. Usher, “You Make Me Wanna…”
Hot 100 Peak Position: 2, Peak Date: October 25, 1997

Here’s a genuine teenage song. “You make me wanna leave the one I’m with,” a 19-year-old Usher Raymond IV sings, willing to trade the good thing he’s got for the uncertainty of a fling. Young folks aren’t the only ones tempted by what’s behind door No. 2, but when you get older, you’re way less likely to play Monty Hall with your heart. It’s called settling, and it’s a beautiful thing.

4. Brandy & Monica, “The Boy Is Mine”
Hot 100 Peak Position: 1, Peak Date: June 6, 1998

Neither singer gives much detail about the guy they’re fighting over, and that says a lot about teenage love triangles. “Must you do the things you do / keep on acting a fool?” sings 17-year-old Monica. “He is a part of my life,” counters 19-year-old Brandy. “I know it’s killing you inside.” The dude is obviously playing them both, high-fiving his boys while they claw and scratch over Dallas Austin and Darkchild’s soap-opera strings and squishy bass sounds. Brandy and Monica ought to key this scrub’s car and then go get coffees.

3. Lorde, “Royals”
Hot 100 Peak Position: 1, Peak Date: October 12, 2013

Even if she’s fascinated by materialistic hip-hop culture, 16-year-old Lorde isn’t striving for Maybachs and diamond watches. “We crave a different kind of buzz,” she sings, speaking for hyper-smart young folks everywhere who may dream of Cadillacs but know there’s more to life.

2. Mario, “Let Me Love You”
Hot 100 Peak Position: 1, Peak Date: January 1, 2005

Being this smooth this young must be some kind of burden. Mario was just 18 when this cool and silky slow jam got all up in America’s business and whispered in its ear, “You should let me love you.” The nation promptly melted into Mario’s arms, and even now, whenever those crisp drums and sensual keyboards—seemingly inspired by “What’s Love Got to Do With It?”—come gliding out over the airwaves, folks of all ages, sexes, and ethnic backgrounds pull over their cars and light up cigarettes.

1. LeAnn Rimes, “How Do I Live”
Hot 100 Peak Position: 2, Peak Date: December 13, 1997

Although Rimes was 15 when this mega-schlocky lover’s plea made its way to radio, it wasn’t members of her peer group that made it a hit. The song’s author, Diane Warren—the queen of overwrought balladry—was 41 in 1997, and the lyrics suggest there’s more at stake (a house, a car, kids) than having a date to the junior prom. This is middle-age desperation via youthful vessel, and all these years later, Delilah listeners still find that combination irresistible.

*Due to changes in chart methodology over the years, certain eras are weighted differently to account for chart turnover rates over various periods.