5 Artists Who Hit No. 1 Late in Their Careers

By Jonathan Hailey

Canadian rapper Drake has been killing it in the music industry since his debut album dropped in 2009. While he recently landed his 100th entry on the Billboard Hot 100 charts, the number one spot has always eluded him.

His latest single “Hotline Bling” is sitting pretty at number two, and Drake shared on his Instagram that if the song hit claimed the top spot during the month of October, his birth month, it would be the biggest moment of his career.

Drake’s post got us thinking about all the artists who were successful, but only got a number one single on the Hot 100 chart after years of trying. Here are five artists who landed their first number one singles well into their careers.

Jay Z – “Empire State of Mind” (2009)

Brooklyn rapper turned business mogul Jay Z has been making some of the most beloved hip-hop music since his debut album Reasonable Doubt in 1996. While he’s reached the top of the charts in album sales consistently, his first number one single didn’t come until 15 years into his career. The ode to NYC with Alicia Keys helped Shawn Carter claim king of the charts for at least a week at the end of the first decade of the new millennium, even though the lyric “concrete jungle where dreams are made of” is nonsensical. We’ll let it slide this time, Jigga.

Taylor Swift – “We Are Never Getting Back Together” (2012)

Now a pop superstar, Taylor Swift debuted as a sweet country girl with a penchant for writing songs that had us staining our guitars with teardrops. Swift had hugely successful singles that snatched the top of the country charts, but she didn’t gain pop success until “We Are Never Getting Back Together,” the lead single off her fourth album Red, was dropped in 2012. Swift should really send a thank you note to whichever ex-boyfriend she wrote this song about.

Justin Bieber – “What Do You Mean?” (2015)

Canadian pop superstar Justin Bieber has had the tween set on lock since 2009. Bieber’s first EP My World boasted the hits “One Time” and “One Less Lonely Girl.” Both songs peaked within the top 20, but both also failed to shoot to number one. Even the ubiquitous Ludacris-assisted track “Baby” didn’t top the charts. However, his latest single “What Do You Mean” helped the singer cross landing a number one off his to-do list.

Alicia Keys – “No One” (2007)

The soul-stirring passion and rawness and honesty in her lyrics made Alicia Keys an instant favorite in 2001. Similar to the other artists on the list, Keys released singles that peaked just shy of the top spot. Her first number one single didn’t come until her third album As I Am. The album’s lead “No One” found the singer/pianist blending her R&B roots with new found pop sensibilities that made for a mid-tempo groove no one could escape.

Teddy Riley (as part of Blackstreet) – “No Diggity” (1996)

Teddy Riley has created hits for everyone from Michael Jackson and Bobby Brown to Heavy D and Guy. His productions for other artists helped them go number one, but Riley didn’t find himself there, as an artist, until his second album with the R&B quartet Blackstreet. Based around a Bill Withers sample, “No Diggity” praised women who played the game of love like a boss and looked good while doing so.

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