25 most popular celebrities of the past 25 years

This story is part of a series to celebrate Yahoo’s 25th birthday. Thanks for joining us along this wild, wonderful ride.

Story continuesThe Kardashian/JennersEven before the 2007 premiere of Keeping Up With the Kardashians, Kim Kardashian was plotting her future as a celebrity, proclaiming in a 1994 home video,"When I'm famous..." Both on-and-off camera, the blended brood of siblings — Kim, Khloe, Kourtney, Rob, Kendall and Kylie — along with matriarch Kris Jenner have endured breakups, motherhood and tabloid scandal, while revolutionizing reality TV, body-positivity, selfies and makeup contouring.

UsherHis self-titled debut album, released when he was 16 years old and one year before Yahoo’s launch, may have stalled on the charts, but since 1997’s six-times-platinum My Way, the R&B singer dancer, actor, entrepreneur, and former Voice coach has made his way to superstar status.

DrakeWho would have thought that the kid who started the millennium as an actor on Degrassi: The Next Generation would become the actual voice of a generation and one of hip-hop’s all-time biggest stars? Over the past decade, Aubrey Drake Graham has blazed a trail with his sensitive-rapper persona, racked up 44 Grammy nominations, headlined Coachella , sold more than 170 million records, and charted more songs on the Billboard Hot 100 than any solo artist in recording history.

Paris HiltonThe heir to the Hilton fortune, Paris Hilton capitalized on her fortuitous lot in life to become famous for doing ... nothing. After an X-rated tape of the socialite was leaked, she parlayed that popularity into becoming a reality TV star on the hit show The Simple Life alongside Nicole Richie. At 38, Hilton has been a pop culture mainstay for most of her life, capitalizing on her name to not only become notorious but a truly successful businesswoman.

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