Drake Makes Anna Wintour Laugh at NYFW Spring 2016, Achieves the Impossible

Drake and Anna Wintour at Serena Williams Signature Collection By HSN
Drake cracks up Anna Wintour at Serena Williams Signature Collection By HSN on Sept. 15 Thomas Concordia/WireImage.com for STYLE360

Drake just proved that nothing is impossible. While sitting front row at rumored girlfriend Serena Williams' Signature Collection by HSN Spring 2016 fashion show on Tuesday, Sept. 15, Drake made famously stoic Anna Wintour crack up, and there's actually photographic evidence.

PHOTOS: The many focused faces of Anna Wintour

Drake and Anna Wintour - NYFW (posing)

The "No New Friends" singer, 28, definitely has a new bud in the fashion industry, judging by the way the Vogue mogul, 65, was smiling.

Drake and Anna Wintour - NYFW (talking)

Wintour, in her signature blunt bob, wore a green, geometric sheath dress with a matching statement necklace and her signature shades to attend the show, while Drake went with an all black ensemble.

Drake and Anna Wintour - NYFW (clapping)

The dynamic duo talked for the entire presentation and were both beaming for the duration of the event.

Serena Williams - NYFW

Williams, 33, wearing a plunging black bodysuit with a black fringe skirt and matching stilettos, revealed that Wintour has been her fashion mentor. "I have been working really closely with Anna and she’s been so amazing helping us out with the whole collection. I have a great team as well," she told Us Weekly at the event.

Gigi Hadid - NYFW

The tennis star's runway was also attended by other certified fashionistas, including model of the moment Gigi Hadid, in a white two-piece crop top and pants with a tan suede trench-vest and nude heels, who sat on the other side of Wintour.

Lily Aldridge - NYFW

Taylor Swift squad member Lily Aldridge also sat front row at the event in a similar color scheme of nude and white, choosing a long, light maxi with a fringe-covered suede jacket, and strappy sandals for the event.

What do you think made Anna Wintour laugh? Tweet with @UsWeekly using the hashtag #stylebyUs!

Sign up now for the Us Weekly newsletter to get breaking celebrity news, hot pics and more delivered straight to your inbox!

Want stories like these delivered straight to your phone? Download the Us Weekly iPhone app now!