+ By Leigh Glenn  + Photos by Nina Kavoossi

Dylan Gilmer has spent about half of his life feeling shy. Considering that he’s just eight years old, that’s a good thing.

Also known as Annapolis rap artist Young Dylan, Gilmer picked up rap easily, memorizing the songs he heard his father playing. “I like lots of rappers, and I started to act them out, kind of,” he says. But he would get nervous when people were around. “ One time, when I was, like, three, my grandmother and grandfather were out here [in the living room], and I was too scared to dance.”

To see Young Dylan today, you’d never guess he’s had anything but oodles of confidence. Since September 2016, he’s been on The Ellen DeGeneres Show four times. Twice, DeGeneres sent him to basketball games—first in Toronto for a Raptors game, where he met Drake, his favorite rapper, and earlier this year to New Orleans for the NBA All-Star game, where he met many of his favorite players, including Stephen Curry, Anthony Davis, LeBron James and Magic Johnson.

DeGeneres’ team found him through the Instagram account that his parents, Damon Gilmer and DeAundra DeJesus, created. Through @officialyoungdylan, they chronicle their son’s rapping, celebrity appearances, sports events, and down time. He has more than 220,000 followers

Gilmer likes to note that he was born the same year that Drake came out with his first recording, in 2009. He enjoys listening to “Trust Issues” and other Drake songs. Gilmer’s mother says that Gilmer doesn’t yet understand all the lyrics, but here and there he picks up something inappropriate. When he performed the DJ Khaled and Drake song “For Free” for DeGeneres and her audience, he “PG’d” the lyrics.

Dylan performing at his Birthday Party. Photo courtesy of the Gilmer Family.

But behind the rap and beyond the bling, there’s still a child who enjoys doing regular kid activities like coloring Marvel characters and playing with Home Alone figures. Yet Gilmer has talent in all areas—from sports (basketball, football, and soccer) to visual arts (he loves to draw), to the stage (he’s studying acting in DC). Thanks to DeGeneres, he met actor Anthony Mackie, who plays Sam Wilson/Falcon in Marvel’s Captain America and Avengers movies.

Mackie taught Gilmer how to make-believe punch—and Gilmer demonstrates the technique with his father, who does not flinch, even though Gilmer comes within inches of his face.

“I want to be Captain America’s son or Black Panther’s son,” Gilmer says of his Marvel heroes. He wouldn’t want anything else if he could just be in a Marvel movie. “Then I’ll be the happiest man in the world,” he says. “I want to be in a drawing book.”

Gilmer gives his imagination room to roam in his play and in his stories.

“I just write stories all the time,” he says. “I like drawing and writing.” He draws to accompany stories—like Home Alone 2 or his own fictional character the Mad Artist. Other drawings include a cousin; one of himself, based on a baby picture; one of his parents, with his mom holding him; designs for shoes; and a self-portrait he gave to DeGeneres.

Many of his drawings also focus on sports. He gave one he drew of Stephen Curry to the Golden State Warriors point guard, and then they shared dance moves on national TV that Gilmer choreographed just for Curry.

Gilmer has a couple of songs coming out soon. “I still have to make a hook, a verse, I mean,” he says—and gives a private demonstration in which his young voice encompasses phrasing and a vibrato that recalls some of the old-school artists he likes—the Temptations, The Jackson 5, and New Edition. (Oklahoma City Thunder point guard Russell Westbrook suggested that he sing when he grows up because “singers get the ladies.”)

Around Annapolis, people know Young Dylan through some of his performances, such as the ones for the Martin Luther King Jr. Day parade, Ignite Annapolis at Maryland Hall, and a Black History Month program at the Stanton Center. He’s heard that his classmates and friends think what he does is cool.

For all of his newfound acclaim, Gilmer remains humble and doesn’t see himself becoming a star. He’s grateful to DeGeneres, who’s said she wants to keep an eye on him as he grows up. “It was really a blessing, and it was fun,” he says, of the experiences with DeGeneres, the basketball players, and Drake.

In his travels, he’s started to see some of the less shiny parts of the world—kids who don’t have parents or homes like his, adults who make their way on the streets of New Orleans or New York. In one of his interviews with DeGeneres, he said he wanted “300 mansions”—one for himself, one for his parents, and the rest to house orphans and poor people.

His parents have their own hopes for him.

“I just want to feed off what he wants to do,” says his father. “I let him sit in on meetings so he can make his own decisions and see what’s going on. I see him being real big . . . not just rap—acting, all different types of things.”

Neither does Gilmer’s mother worry too much about what he does. “[Just that] whatever he does, whether rapping or acting, he’s happy and he gives back like he says he would,” she says.

Above all, Gilmer is grateful for his family. “They put me up for something that I get nervous for, and they help me a lot and they teach me more, and teach me not to do bad stuff,” he says. “When I hit a song right, they get proud of me, and that gives me more confidence.”