Stefan Alexander covers Tweet/Missy Elliot classic “Oops (Oh My)”

NYC-based queer pop artist Stefan Alexander, whose promising initial surge began three years ago with his debut single “Skeleton,” has released a video for his cover of Tweet’s “Oops (Oh My)” feat. Missy Elliot.

“Back when I was a kid, the song (and the iconic music video) felt so scandalous in the best way possible,” says Alexander. “Now, from an adult perspective, I understand the lyrics to be about self-pleasure and independence, especially for women and femme-identifying folks, who are too often stigmatized for their sexual desire. The message is timeless!”

Stefan grew up in an artistic household in Northampton, MA playing multiple instruments including cello, piano, guitar and mandolin. While attending NYU’s Clive Davis program, he formed a folk band opposite pop singer Phoebe Ryan. In the NYC folk clubs, Stefan honed his songwriting and vocals, realizing his strengths as a pop musician. Stefan soon began collaborating with producers Elliot Jacobson (Verité, Elle King) and Andrew Horowitz (John Legend, Janelle Monae) to discover his sound.

With his smooth as silk vocals laid over a very stylized R&B bed, Stefan switches up the perspective, tackles the track, and posits it in a very modern take, while maintaining all of the flavor. Replacing the sparse Timbaland production with a more synth-driven texture, he embraces all of Tweet’s sensual delivery and turns up the heat, making the song more intimate and seductive.  

Tackling such an iconic song is no easy feat, and Stefan told Stitched Sound, “I tried to modernize the song with some more current production, but I wanted to stay true to the original as much as possible. The most important thing was to keep the sensuality of the original, so hopefully that comes through.”

Although his career trajectory was cut short when he succumbed to a mysterious pain disorder (Central Sensitization Syndrome) that made it impossible for him to perform music, much less most physical activity, Stefan has picked up where he left off. He is using his platform to speak honestly about his chronic illness and hopes his story can inspire others to overcome whatever challenges they may be facing in their lives.

Back in the ring, Alexander released the much-lauded EP Thunderclap earlier this summer, signaling his return to form, of which The New Nine said, “An emotional pop masterpiece that will get stuck in your head but also make you cry if you let it sneak up on you.”

Stefan plans to release his second EP in early 2020, with more music coming throughout the spring and summer.