SHANE MICHAEL SINGH Award-winning Journalist. Content Strategist. Storyteller. Big Brand Enthusiast.

As the Executive Editor of Playboy's Winter 2019 issue, I led Playboy's editorial team in producing one of the buzziest moments in recent company history: a cover featuring Kylie Jenner produced by Travis Scott. The cover image, shot by Sasha Samsanova, was unexpected in that it did not feature the "self-made billionaire's" face — a strategic decision to ensure Playboy's masthead remained front and center as the vanguard of that issue's unifying theme: Pleasure For All. Kylie Jenner's cover led an issue that also featured Broadway wunderkind Jeremy O. Harris, commentator Anand Giridharadas, actor Thomas Middleditch, pop ingenue King Princess, New York Times best-selling author Lisa Taddeo, cultural critic Jelani Cobb, modern music maestro Toro y Moi, and legendary artist Marilyn Minter. The issue generated billions of media impressions and inspired new jewelry and apparel collections, sold exclusively on Playboy.com.