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(In 2018, the Billboard staff released a list project of its choices for the Greatest Pop Star of every year, going back to 1981 — along with a handful of sidebar columns and lists on other important pop star themes from the period. Find one such sidebar below about how Drake and Kid Cudi evolved the sound and feeling of hip-hop at a crucial turning point in pop, and find our Greatest Pop Star picks for every year up to present day here.)
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By the end of the ‘00s, hip-hop’s long held line of demarcation between rapping and crooning was blurry as ever. With their ambition and vulnerability, Kid Cudi and Drake erased it completely.
Like many paradigm shifts in millennial culture, this revolution is impossible to separate from Kanye West. Reeling from his mother’s death, Kanye’s embrace of Auto-Tune and anguish across 2008’s 808s and Heartbreak is frequently credited for the rapper-singer sea change, though he wasn’t without his forerunners — there was Nelly, there was T-Pain, there was “Lollipop,” there were countless others. But it was an upstart Cleveland MC who shaped 808s most of all.
The moody melodicism of debut mixtape A Kid Named Cudi led to the 24-year old co-writing four 808s tracks and scoring a deal with Kanye’s G.O.O.D Music imprint. Soon, the words “emo” and “rap” fused like checkers on Vans. Cudi’s debut single “Day ‘n’ Nite,” inspired by the death of his uncle, unrequited love, and his nocturnal weed habit medicating it all, went top-five in May 2009. Studio debut Man on the Moon: The End of Day went on to break 100,000 in first-week sales and nab three Grammy nominations before the year was out. It was a rap album that welcomed intrepid indie groups like MGMT and Ratatat, a novel concept at the time. It’s no accident a couple intrepid indie-rap groups would be lurking around the corner.
While Kid Cudi’s rise was deeply intertwined with Kanye, Drake was the first 808s disciple to become a star from outside G.O.O.D’s orbit. The Toronto native — just two years removed from Degrassi — sparked a major label bidding war behind his 2009 mixtape So Far Gone, eventually won by Lil Wayne’s Young Money empire that June. While Cudi’s lyrics confronted depression, addiction and mortality, Drake emoted less-harrowing 20-something concerns regarding fame, women and famous women. Soon, he’d reach a level of fame Cudi only hinted at. His velvety No. 2-peaking breakthrough hit “Best I Ever Had” serenaded a flame from back home as if she was already a celebrity. Twelve months earlier, the same sort of rap-R&B hybrid smash would have required a T-Pain or an Usher alongside a Weezy or Jeezy; now there was Drake, and only Drake.
While Cudi and Drake went down strikingly different career paths in the years that followed, their collective influence proved ubiquitous. Artists like Frank Ocean, Childish Gambino, Chance the Rapper, J. Cole, Juice WRLD, and a host of others were free to rhyme or croon their way across the sonic and emotional spectrum — making the case with their ballooning success that rap music had simply become the new pop music of the 2010s.
(Read on to our Greatest Pop Star of 2010 here, or head back to the full list here.)