In the ever-evolving world of pop music, few achievements truly stand the test of time. Chart-topping singles come and go, but there are rare moments in history when an artist not only dominates the Billboard Hot 100 but does so with such consistency and power that they break records and set new standards for global success. Only three artists have accomplished one of the most elite feats in music history: scoring more than three No. 1 singles and five charting hits from the same album. That legendary trio? Madonna, Michael Jackson, and Katy Perry.
This exclusive club is not just a testament to commercial success, but to cultural impact, innovative artistry, and a masterful understanding of the pop music landscape. Each artist did it in their own era, in their own way—and in doing so, they changed the game forever.
🔥 Michael Jackson – Bad (1987)
Chart-toppers from the album:
- I Just Can’t Stop Loving You (with Siedah Garrett) – #1
- Bad – #1
- The Way You Make Me Feel – #1
- Man in the Mirror – #1
- Dirty Diana – #1
Other Hot 100 hits from the album:
- Another Part of Me – #11
- Leave Me Alone – charted internationally
Michael Jackson set the gold standard for this level of chart domination with his 1987 masterpiece, Bad. The King of Pop became the first artist in history to land five No. 1 singles from the same album—a feat that was unheard of at the time and remained untouched for decades. Building on the massive success of Thriller, Bad showcased Michael’s versatility, showmanship, and unique ability to blend pop, rock, and R&B in a way that was universally appealing.
Notably, Bad was the first album ever to produce five Hot 100 No. 1s, solidifying Jackson’s legacy as a generational talent. It wasn’t just the music—it was the videos, the dance, the image, and the cultural moment. Michael Jackson didn’t just release singles—he created events.
👑 Madonna – True Blue (1986)
Chart-toppers from the album:
- Live to Tell – #1
- Papa Don’t Preach – #1
- Open Your Heart – #1
Other Hot 100 hits from the album:
- True Blue – #3
- La Isla Bonita – #4
With her third studio album True Blue, Madonna cemented her place not just as a pop star, but as a global phenomenon. Released in 1986, True Blue saw Madonna evolve thematically and sonically, showcasing a newfound maturity in both lyrics and production. It became the best-selling album of the year worldwide and catapulted her into the pantheon of music royalty.
Although she fell just short of five No. 1s from the album (with three #1s and two additional Top 5 hits), True Blue was a juggernaut on the charts. The album’s ability to produce five Top 5 hits from a single record—three of which topped the chart—placed her in the upper echelon of Hot 100 history.
Madonna’s feat is especially notable because she achieved it during a time when women were rarely granted the same radio play or industry support as their male counterparts. Her success with True Blue broke barriers for female pop stars and made her a blueprint for generations to come.
🌈 Katy Perry – Teenage Dream (2010)
Chart-toppers from the album:
- California Gurls (feat. Snoop Dogg) – #1
- Teenage Dream – #1
- Firework – #1
- E.T. (feat. Kanye West) – #1
- Last Friday Night (T.G.I.F.) – #1
Other Hot 100 hits from the album:
- The One That Got Away – #3
- Wide Awake (from Teenage Dream: The Complete Confection) – #2
- Part of Me (from Teenage Dream: The Complete Confection) – #1
Fast forward to 2010, and Katy Perry made history by matching and even expanding on Jackson’s achievement. With her sophomore pop album Teenage Dream, Perry became the first woman and second artist ever to land five No. 1 singles from one album, tying Michael Jackson’s record from Bad.
The era was a pop culture explosion—colorful wigs, candy-themed videos, and radio-ready anthems that blended playfulness with empowerment. Perry didn’t just top the charts—she dominated them for months at a time. The album was a commercial and critical juggernaut, and the singles each came with viral music videos, high-energy performances, and enormous cultural traction.
With the reissue of the album (Teenage Dream: The Complete Confection), Perry scored additional hits like Part of Me and Wide Awake, both of which became Top 3 singles—further extending the album’s legacy.
A Rare, Timeless Achievement
To be clear: many albums produce hit songs, and a handful yield multiple No. 1s. But to score five singles in the Top 5, with three or more of them reaching #1, all from the same project, is an achievement that requires:
- Masterful songwriting and production
- Relentless promotion and performance
- A deep connection with fans and the cultural moment
That’s what makes this trio so exceptional.
- Michael Jackson did it first, with artistic vision and a global pop movement.
- Madonna did it by breaking the mold and building a cultural empire.
- Katy Perry did it by turning pop music into a visual, vibrant, and emotionally resonant phenomenon.
Each did it in a different era—pre-digital, CD-era, and streaming age. Each reached the pinnacle of chart success in the face of industry changes, critics, and evolving audiences.
Legacy and Influence
These artists didn’t just dominate the charts—they reshaped what we expect from pop albums.
- Michael Jackson’s Bad became the gold standard of pop performance and set a bar no one thought could be reached.
- Madonna’s True Blue gave pop music a sophisticated female voice at a time when that was a rarity.
- Katy Perry’s Teenage Dream ushered in a new era of digital-age pop, one that merged memes, music, and marketing with millennial optimism and raw vulnerability.
The artists who join or even come close to this league in the future will do so with full knowledge of the icons who laid the groundwork.
Final Thoughts
In a music industry driven by trends and short attention spans, very few projects achieve a lasting legacy. But for Michael Jackson, Madonna, and Katy Perry, these landmark albums weren’t just momentary successes—they became cultural blueprints.
Three legends. Three different decades. One rare feat.
More than three No. 1s. Five hits from a single album.
That’s pop history.
