Why did Cindy Sherman make herself up as a clown? What has Diana Ross, Donatella Versace and Dita Von Teese revealed about their notions of beauty? And why is a skateboard on A+R founder Rose Apodaca's lip? Rose has a lifetime of observations and experience to spill, and spill she will when she's interviewed this Friday, May 10, on @MACpro LIVE at 3pmPST with Gregory Arlt, beauty influencer, celebrity makeup artist and director of makeup artistry for M•A•C Cosmetics.

Gregory and Rose go back at least a decade and a half to when he was a senior makeup artist for the brand and she was west coast bureau chief for fashion and beauty industry bible Women's Wear Daily. This chat is part of MAC Pro's ongoing series on Instagram LIVE with beauty pros, tastemakers and (in the case of Rose) journalists.

The Los Angeles native has devoted half his life to making up beautiful women across all media. In 2015, he won the prestigious Hollywood Beauty Award for Best Makeup Artist. He has worked backstage in Milan, Paris and New York for the likes of Alexander McQueen, Oscar de la Renta, Michael Kors and Chloe, among other fashion houses. And widely known as the "Beauty Exorcist," he is now working with photographer Steve Earle and his wide coterie of celebrity pals on his first book.

Gwen Stefani, Angelina Jolie and Katy Perry are among the famous faces Gregory regularly glamorizes. He is also one of the only makeup artists in the world that Dita Von Teese feels comfortable with doing her face when she personally opts out. On that note, Gregory was one of few guests included in "The Ultimate Guide to Eccentric Glamour," The New York Times best-seller by Dita and Rose.

Expect a lively reveal when the pair go live on @MACpro LIVE on Instagram this Friday, May 10, at 3pmPST.