This is a small time machine. A chart-topping single appears, then four artists. You point to the singer that actually took it to number one. That’s the whole bit.
Sounds jump lanes. Club heaters, coffeehouse whispers, blog-rock buzz, bilingual earworms. YouTube arrives, downloads surge, but the crown still feels huge each week.
Let the first beat hit. If the name clicks before the reasons, good. If two names tug, picture the video or the album cover. Then decide and keep rolling.
[D] Shakira | Wyclef Jean's production mixed cumbia with reggaeton, creating the World Cup's soundtrack while Shakira's truthful hips conquered global charts.
2/25
Crank That?
[D] Soulja Boy Tell'em | The 17-year-old's YouTube dance instruction video revolutionized music marketing while steel drums made everyone Superman that movement.
3/25
SexyBack?
[C] Justin Timberlake | Timbaland's industrial beats transformed the former boy bander into Prince's heir while falsetto "yeahs" became everyone's catchphrase.
4/25
Bleeding Love?
[C] Leona Lewis | Simon Cowell's X Factor winner brought British talent shows stateside credibility while Ryan Tedder's production created vocal Olympics.
5/25
Amazed?
[B] Lonestar | This country crossover spent eight weeks atop both country and pop charts, becoming wedding DJs' most requested slow dance anthem.
6/25
Stand Up?
[B] Ludacris | Featured in 2 Fast 2 Furious, Luda's Southern party anthem proved Atlanta's grip on hip-hop while introducing mainstream audiences to crunk.
7/25
Girlfriend?
[C] Avril Lavigne | The pop-punk princess's cheerleader anthem sparked plagiarism lawsuits while its multilingual versions conquered international charts simultaneously.
8/25
Family Affair?
[D] Mary J. Blige | Dr. Dre's minimalist production helped the Queen of Hip-Hop Soul celebrate leaving drama behind while ironically creating timeless drama-free party music.
9/25
Butterfly?
[C] Crazy Town | Sampling Red Hot Chili Peppers' "Pretty Little Ditty," these rap-rockers created nu-metal's softest hit before vanishing into one-hit wonder territory.
10/25
Ms. Jackson?
[A] OutKast | André 3000's apology to Erykah Badu's mother became OutKast's highest-charting single, mixing Southern hip-hop with unexpected harmonica solos.
11/25
I Believe?
[A] Fantasia | The single mother's emotional Idol victory song showcased church-trained vocals that Simon Cowell called the best performance in show history.
12/25
Womanizer?
[D] Britney Spears | Post-breakdown Britney's robotic comeback proved tabloid scandals couldn't kill pop royalty while "womanizer-izer-izer" became oddly hypnotic.
13/25
Foolish?
[D] Ashanti | Sampling DeBarge's "Stay With Me," this heartbreak anthem spent 10 weeks at #1, establishing Ashanti as R&B's new princess.
14/25
London Bridge?
[B] Fergie | The Black Eyed Pea's solo debut interpolated "Oh Snap!" while her spelling bee bridges made nursery rhymes surprisingly provocative.
15/25
Goodies?
[C] Ciara | Produced by Lil Jon, the Atlanta dancer's debut introduced crunk&B while her matrix-defying moves made "1, 2 Step" unforgettable.
16/25
Do I Make You Proud?
[C] Taylor Hicks | The grey-haired Soul Patrol leader's Idol victory proved America preferred harmonica-playing dad rock over contemporary pop.
17/25
Bump?
[D] B2K | P. Diddy's protégés rode this Rodney Jerkins production to #1 while Chris Stokes controversies quietly brewed behind their squeaky-clean image.
18/25
Laffy Taffy?
[A] D4L | Atlanta's snap music peaked when this candy-themed innuendo outsold everything, proving ringtone sales could determine chart positions.
19/25
Run It!?
[B] Chris Brown | At 16, Breezy's Jive Records debut made him the first male artist since Montell Jordan to top charts with their first single.
20/25
Always On Time?
[C] Ja Rule | Featuring Ashanti's silky vocals, this Murder Inc. collaboration dominated urban radio while Ja ruled hip-hop before 50 Cent's arrival.
21/25
Bad Day?
[D] Daniel Powter | Used in American Idol's elimination montages, this Canadian's one-hit wonder became 2006's best-selling single through reality TV tears.
22/25
Let Me Love You?
[B] Mario | The Baltimore teenager's Scott Storch-produced slow jam proved R&B could still dominate charts during hip-hop's commercial peak.
23/25
This Is Why I'm Hot?
[D] MIMS | The New York rapper's circular logic about hotness somehow topped charts while becoming hip-hop's most mocked yet successful single.
24/25
Incomplete?
[D] Sisqo | The Dru Hill frontman's solo debut about thongs became 2000's most unlikely crossover, spawning countless parodies and cementing underwear in pop culture.
25/25
This Is The Night?
[D] Clay Aiken | The Idol runner-up shocked everyone by debuting at #1, outselling winner Ruben Studdard and spawning the devoted Claymates fanbase.