Who Took Lenny Williams’ Drawers?

You ever fall for some clickbait, and later find out it’s actually a heartwarming example of intergenerational connection and the beautiful legacy of Oakland?

It’s the darnedest thing, and it happened to me earlier this week.

After the social media accounts for Lenny Williams, famed singer and former frontman for the funk band Tower of Power, dropped a video for his new song, “She Took My Drawers,” I was on the other end of the internet starring at my phone in disbelief.

Wha… Why? Why would the legendary vocalist who brought the world timeless songs like “‘Cause I Love You” and “So Very Hard To Go” be singing about extramarital affairs and blackmail via stolen underwear!?

The song’s first verse establishes that the protagonist had fallen asleep in a hotel bed with a woman who is not his wife, and woken up alone. In short order, he realizes that the woman took his underwear before she left, and she begins to threaten to post them online.

These are not just any ordinary underwear, according to the second verse:

These boxers are special, a gift from my wife to me
As a symbol of our love on our 21st anniversary
Had her picture on the front, and mine on the back
Lawd have mercy, I’m ’bout to have me a heart attack

Who wrote this? Who put this together? Whose idea was this?

I felt bad for watching it. Then, naturally, I shared it through a few texts and social media posts. I got ready to move onto the next meme, chalking it all up to Lenny Williams entering his ‘do it for the gram’ phase, when a few folks scattered across the country hit me up. They had questions too — “Why?” being the main one.

So I reached out to Lenny Williams’ social media account, and within five minutes I heard back from someone who said we’d met a couple of times over the years — a guy by the name of Dwayne Davis — Lenny Williams’ grandson and main representative.

Dwayne! In 2019, he was a senior at McClymonds High School, we talked about the school’s closure due to trichloroethylene (TCE) in the groundwater. We crossed paths again in 2021 when I hosted a panel discussion for Pete Nicks’ documentary film about the Oakland Unified School District, Homeroom; Dwayne was one of the co-stars of the film.

And now look at him, after internships with powerhouse media companies Proximity Media, XTR Media and MACRO, as well as a stint with WACO Theatre, founded by Richard and Tina Knowles-Lawson, Dwayne landed in Los Angeles. Now he’s managing artists, including his grandfather on his mom’s side.

Not only is he representing Williams behind the scenes, he also played the role of young Lenny in the music video for “She Took My Drawers.”

During a phone call, Dwayne confirms that Lenny did indeed write the song, with assistance from Derek “DOA” Allen. The video was directed by another family member, Jamal Josef.

“It’s had mixed reception online,” Dwayne tells me. There have been some negative comments, but friends, family and fans at shows seem to love it.

“It’s raunchy and fun,” Dwayne says, adding that it’s a nod to the storytelling style of modern southern soul, something that Lenny has been experimenting with while currently on tour with artists like Tucka and Pokey Bear (whose similarly themed song “My Side Piece” has 68 million views on YouTube).

Still, Dwayne confirms, “People are stunned that it’s the same man who sang “‘Cause I Love You.” Dwayne says seeing the audience’s reaction is one thing, but traveling with his grandfather on tour is a whole story within itself.

“I learn so much, experience so much, and every show is a quick turnaround,” says Dwayne, adding that they only do performances on the weekend, and stay in each city for less than 24 hours: “We’re usually on the first flight in and first flight out.” The majority of the shows are in the south or on the east coast.

“Meeting artists, promoters and fans around the country has been life-changing,” says Dwayne, a 21 year-old who aspires to be in the entertainment industry. “I feel like I’m getting my bearings and learning how everything works.”

When Dwayne was six, he recalls being on a big boat with friends and family, taking photos with his grandfather. Moments later, Grandpa was on stage as the Lenny Williams. “Seeing the crowd so entertained, it was a foundational moment; that’s when it clicked,” says Dwayne. “Not just him being who he is, but that I wanted to be up there too. I wanted to entertain.”

Dwayne is on his path, but he knows he’s got a lot of ground to cover to match the legacy of his grandfather, who was inducted into the Rhythm and Blues Hall of Fame in 2017.

“He’s my biggest motivation in human form,” says Dwayne, humbly. “I want to make him proud.”

Lenny Williams performs Friday, March 15, at the Paramount Theatre in Oakland as part of the 2024 Blues Is Alright Tour. Details here.