Toronto Raptors superfan, global rap icon, and sometimes poet Drake has made headlines for countless reasons, but his over-the-top ESPYs love confession to WNBA star Skylar Diggins-Smith in 2014 remains a highlight reel of awkwardness. From “Can I Digg In” poems to a lipstick-stained forehead kiss, this saga had everything—comedy, cringe, and a boyfriend watching it all unfold. Let’s break it down.
Drake’s Poetic Disaster: “Can I Digg In?”
It all began at the 2014 ESPYs, where Drake decided to showcase his poetic side. Standing on stage with the confidence of a man who’s written platinum albums, he launched into a heartfelt (and questionable) rhyme titled “Can I Digg In.” Dedicated to then-Dallas Wings star Skylar Diggins-Smith, the poem was less Shakespeare and more middle-school-crush vibes.
The lines weren’t just cheesy—they were Gouda-level:
“Oh wow, Lordy Lordy, Michael Jordy!” Yes, that’s an actual line. No, we don’t know why.
As Drake bared his metaphorical soul, Skylar herself crept up behind him, ready to steal the spotlight (and maybe salvage the moment). “Oh my god!” Drake exclaimed when he noticed her. Shocked, flustered, and fumbling to justify his poem, the rapper found himself in the middle of a bit that quickly turned into an unintentional roast.
Lipstick and Laughs: The Forehead Kiss Heard Around the World
Visibly unimpressed, Diggins-Smith put an end to the chaos with one simple question: “What’s it going to take to stop this craziness?” Drake, channeling his inner rom-com hero, responded, “A kiss.” Bold move, Drizzy.
In a twist straight out of a sitcom, Skylar agreed—but with a catch. She told Drake to close his eyes, leaned in as if going for a romantic kiss, and instead planted a dramatic peck on his forehead, leaving behind a bright red lipstick stain. The crowd roared. Drake? Probably less so.
Adding to the tension? Skylar’s then-boyfriend (now-husband) Daniel Smith sat in the audience, surely having the most uncomfortable night of his life. Let’s not forget their Instagram spat with Drake beforehand. The result? A moment so awkward, it’s still being replayed in cringe compilations everywhere.
Bayou Barbie’s Take: “Skylar Walked So We Could Run”
Fast forward to January 2025, and Skylar Diggins-Smith is back in the headlines, thanks to Chicago Sky star Angel Reese—better known as “Bayou Barbie.” On her podcast Unapologetically Angel, Reese crowned Diggins-Smith as the WNBA’s original “baddie.”
“How was it being credited as the first W baddie?” Reese asked during the show, clearly eager to give Skylar her flowers. Diggins-Smith, ever the humble queen, brushed off the title with a laugh, saying, “No, no, I don’t care. I think that’s cool.”
Reese, however, wasn’t done hyping up her fellow star. She credited Diggins-Smith for paving the way, proclaiming, “You walked so we could run.” A fair point—Skylar’s mix of talent, style, and swagger made her an icon both on and off the court.
From Poetry to Praise: Skylar’s Legacy
Skylar Diggins-Smith’s career has been nothing short of legendary. From roasting Drake on live television to earning the title of the WNBA’s first baddie, she’s proven she can handle it all with grace, humor, and a killer game.
