RuPaul's relationship with drag queen Raven began on Season 2 of "RuPaul's Drag Race" when Raven was a contestant (via Cosmopolitan). While she didn't win the season, Raven certainly made an impression.
She was the runner-up and eventually returned to the "Drag Race" workroom on Season 1 of "RuPaul's Drag Race All-Stars." Again, she was the runner-up, but her time with RuPaul was far from over.
Now, Raven serves as RuPaul's makeup artist on "RuPaul's Drag Race" and its spin-off shows. When Ru's longtime makeup artist, Mathu Anderson, quit during the filming of "Drag Race" Season 9, Raven stepped in to fill his shoes (via Out). Now, the MUA has won an Emmy for her work on the show and even serves as a creative producer.
Raven and Ru have a special relationship, which can be seen in Raven's Instagram post about her Emmy win. "I am forever grateful to @rupaulofficial for trusting me enough to step 'behind the curtain' and do something so few have. Even after my nerves got the best of me, I made, what I deem, a disaster of that mug for an entire season, he called me back for the next. Keeping that faith and trust in me means the world."