All About His Sons and Daughters

Rickey Smiley takes pride in being a father.

The radio personality and stand-up comedian is a dad to six children. His adult kids include D’essence, Malik and Aaryn. His eldest son, Brandon, died in January 2023 of an accidental drug overdose. One year later, Rickey discovered that he was a father to twin daughters, Allyson and Allyssa, though he didn’t share the news until January 2025.

Rickey is prolific on social media, sharing snapshots of his life on his personal Instagram, as well as bringing his children onto his radio show, The Rickey Smiley Morning Show. Several of his kids, including his eldest children Brandon and D’essence, also appeared on his unscripted reality TV series Rickey Smiley for Real.

During a June 2018 interview with Rolling Out, Rickey shared what he hoped the legacy he was leaving for his children would be, telling the outlet, “You have to play no games.”

“I hope that I leave something positive with them to make them want to be the best that they can be,” he said. “I hope they take what I have taught them and apply it when it comes to their kids. Because they too will be parents one day, as well.”

Here’s everything to know about Rickey Smiley’s kids: late son Brandon, D’essence, Malik, Aaryn, Allyson and Allyssa.

Brandon Smiley

Rickey welcomed his oldest son, Brandon, on Feb. 7, 1990.

The radio personality and Brandon’s mom split when he was an infant. Brandon moved in with his dad when he was in the eighth grade, and Rickey described his son as the “big brother” and “caretaker” for his younger siblings in a May 2023 interview with PEOPLE.

“When he got his driver’s license, he took them everywhere: movies, the amusement park,” Rickey recalled.

After graduating high school, Brandon attended Alabama State University before transferring to the University of Alabama, though he ultimately did not finish college.

Rickey said his son was “hard-working” and had a job at a landscaping company in addition to following in his footsteps as an aspiring comedian. The father-son duo appeared on the unscripted TV series Rickey Smiley for Real from 2015 to 2018.

Brandon died at age 32 of fentanyl and ethanol toxicity on Jan. 29, 2023, after a years-long struggle with an addiction to painkillers. Rickey, whose father died of a drug overdose when he was young, spoke to PEOPLE in March 2024 about the heartbreaking experience of the death of his son.

“It’s your 32-year-old son that died, but man, you start thinking about your 5, 6, 7, 8, 9, 10, 11, 12-year-old son,” he explained. “You’re thinking about the birthday parties at Chuck E. Cheese, you’re thinking about the kid that slept in the bed with you, that you helped get dressed and brush his teeth.”

Rickey added, “That’s your child. I felt it from top to bottom, inside to outside.”

He still experiences “triggering” moments when he hears a song that reminds him of Brandon, but he also looks to his own memories, including funny videos of his son.

“I just look at it and laugh and it sort of keeps him alive, but it doesn’t send me to a dark place,” Rickey shared. “I just kind of smile and laugh as if he’s still living.”

D’essence Smiley, 27

Rickey’s second child, daughter D’essence Elizabeth Smiley, was born on Aug. 2, 1997.

After graduating from high school, D’essence revealed in a May 2016 broadcast of The Rickey Smiley Morning Show that she was a freshman at Florida International University.

She transferred to Tennessee State University and told her dad in a November 2020 YouTube video how she balanced her college classes while working at Amazon and Panera Bread seven days a week.

D’essence graduated from TSU in May 2021, with her dad cheering her on from the crowd and capturing the special moment in a video shared on Facebook.

Over the years, D’essence has appeared on her dad’s reality TV series Rickey Smiley For Real alongside her siblings. She is also a business owner and founded The D’essence Collection, a sunglasses brand that was previously featured in several Atlanta pop-up shops.

D’essence is also a mom. She welcomed her daughter, Denver Elizabeth, in December 2022.

Malik Smiley, 23

Rickey’s third child, son Malik, was born on May 17, 2001.

In a March 2019 panel, Malik spoke about his experience growing up with a father in the spotlight, explaining, “As a kid, if your dad is famous, you would feel special, and you would tell people. But as I got older, I grew out of that, and you don’t want that attention.”

After a stint in military school, Malik graduated high school from IMG Academy in June 2019, as shared by his father in a Facebook video.

He followed in his dad’s footsteps and attended Alabama State University for college, where he was a member of the school’s basketball team. Malik graduated from college with honors in December 2023, a moment that was documented on his father’s YouTube channel.

Before doing so, he shared his plans for post-grad in a November 2023 taping of The Rickey Smiley Morning Show, telling his dad on-air that he wanted to attend grad school and then law school. Malik revealed that his goal was to practice law, specifically focusing on criminal law and personal injury and criminal. Malik also said that he’d consider modeling if the opportunity presented itself.

In response, Rickey expressed his pride in his son’s accomplishments.

“I just want to say that you work really hard. I just want to thank you for everything,” he said. “There’s not enough time in the world on this radio to express.”

Aaryn Smiley, 23

Rickey welcomed his fourth child, daughter Aaryn, on July 3, 2001.

Before she graduated high school, Aaryn lived in Bogotá, Colombia, with her mom. Aaryn opened up about her time abroad in a March 2019 panel, sharing that she liked it more than the United States. “I made a lot of friends, I was on the volleyball team, I was finishing my sophomore and junior year,” she said.

Aaryn graduated from high school in Houston in May 2019 and went on to attend Baylor University, where she was a member of the sorority Alpha Kappa Alpha Pi Mu chapter.

While she was in college, Aaryn worked at Starbucks. Her dad documented her first day on the job in an Instagram post in May 2020. Rickey shared that Aaryn, D’essence and Malik had experience working in the restaurant business.

Around this time, Aaryn was shot multiple times in Houston in a drive-by while she was grabbing food and was hospitalized in July 2020. A bullet entered and exited her left leg before getting lodged in her right.

Aaryn spoke about the incident on The Rickey Smiley Morning Show, recalling how she didn’t realize she had been shot in the legs until her boyfriend pointed it out.

Fast forward to August 2023, Aaryn graduated from Baylor University with a B.S. in communication sciences and disorders with a concentration in speech pathology. During her undergrad, she envisioned attending grad school and eventually opening up her own speech clinic for children.

Rickey shared that he was “so proud” of his daughter for her accomplishments and celebrated accordingly. After Aaryn’s graduation, he hosted a private dinner at a comedy club, followed by karaoke.

Allyson and Allyssa, 5

Rickey’s youngest daughters, twins Allyson and Allyssa, were born on Feb. 1, 2019.

The comedian didn’t discover he was their father until January 2024. A year later, during a January 2025 appearance on the Smitty & Dee podcast, he recalled receiving a phone call from his ex-girlfriend — who he remained friends with after their split — telling him that he was the father. The moment came after she went to court with one of her ex-boyfriends and learned that Rickey was her daughters’ dad.

Rickey said that his family “lost it” when he surprised them with the news, which came one year after his son Brandon died. Today, he describes them as “one big happy family.”

He sees the resemblance between himself and his daughters, too. “One of them looks like me when I was 5, and the other one has my personality,” the stand-up star said.

Rickey has shared several videos of his daughters on social media since announcing the news, including an adorable clip from Christmas Eve that he posted in January 2025, teasing them about Santa Claus. He also captured the moment they took their first flight the previous year while on their way to Disney World.