11/15/2025
Story Time: How I Got to DJ Sasha Obama’s Sweet Sixteen Birthday Party
One morning, I get a phone call from an unknown number. Of course, I don’t answer — if they want me, they’ll leave a voicemail. And that they did. I check it, and I hear a familiar name and voice. After I get myself together, I call her back.
She goes, “Hey Mr. Johnson, how have you been? How are things with you?”
I catch her up on what’s been going on in my life, then I ask her the same: “What’s going on with you? How have you been? How’s your mom?”
She tells me everything and everyone is good.
So then I ask, “What’s up? What’s going on? How can I help you?”
She goes, “Well, I’m working for the Obamas now as Mrs. Obama’s executive assistant.”
I’m on the other end like 😳. I’m thinking, Not the sixth grader who was a student in my Young Ladies and Gentlemen’s Club at Horace Mann Middle School where I worked!
I said, “Stop playing.”
She says, “No, Mr. Johnson, for real — I work for the Obamas.”
“So you be on Air Force One?”
“Yes.”
“So you be at the White House… like the Oval Office? The West Wing?”
“Yes.”
“The helicopter?”
“Yes.” 👀
Then she goes, “Mrs. Obama doesn’t move without me.”
My face: 😲
She goes on to tell me they were looking for a DJ for Sasha’s Sweet Sixteen.
I said, “I’m available!” before she could even ask, lol.
She said she told them about me — how I used to DJ at our school events and the Young Ladies and Gentlemen’s Club. Mrs. Obama wanted to know more, so she told her I also DJ for Timbaland and Justin Timberlake.
Her face: 😳
I asked if they had a date, and she said they were throwing different dates around. I told her the only thing I had coming up was my birthday party in Las Vegas on May 14.
She said, “Oh yeah, I told her about how every year for your birthday, you’re in a different city or country with Justin.”
I said, “Yeah.”
She goes, “Okay, I’ll give them the information and get back with you. Oh yeah — another DJ’s name came up too, so we’re going to see, and I’ll let you know.”
I said, “Cool, no problem. Just let me know.”
She goes, “Oh wait, one more thing — how much would you charge?”
Before she could take her next breath, I said, “Charge for what? That’s free.”
She said, “Okay, I’ll call you back for real this time. Bye.”
About two weeks go by, and I get another phone call. They were in Indonesia on vacation — you know, the infamous picture where Barack had his shirt off in the ocean? Yeah… they called me from over there.
She goes, “How you doing?”
I said, “I’m good. I hope you got some good news for me.”
She says, “Yes — Mrs. Obama and Mr. Obama picked you to be the DJ.”
I said, “Can I ask why?”
She said the other DJ was asking for an arm and a foot, and wanted equipment shipped from another city to D.C. I said, “All I need is three plane tickets and I’m good.”
She said, “Okay, deal.”
In the midst of all that, Brittney knew about it and her mom knew about it. Her mom even said, “YOU BETTER NOT BE TAKING NO SCALLYWAG. 😂🤣😂 It’s me, you, and Britt.”
Me: 🤷🏾♂️😂
Anyway, because it involved the presidency, we couldn’t talk about it. Nobody could know.
Finally, I get another call. She goes, “We decided to do the party on May 13, so we’re going to fly you in on the 12th. The party will be on the 13th, and then we’re flying you to Las Vegas for your birthday as a gift.”
I said, “Well, thank you!”
We get to D.C., and the party is at the Kennedy Center. I asked my girl, “Hey, can we get a picture?” She goes, “Oh yeah, y’all will take pictures, no problem.”
So we’re in the green room, and I ask her what time they’re coming. She says 7:45. Then there’s movement, and Secret Service closes the door. Then he opens it and says, “Freestyle, come outside and stand right here against the wall.”
At 7:45 on the dot, the elevators open — and out come Mr. Obama, Mrs. Obama, Mrs. Obama’s mom, and Sasha.
Mr. Obama walks right up to me and says, “Hey Freestyle, how are you doing?”
Inside I’m like, How do you know me? How do you know all this?
Because he was saying little things that let me know they had done their homework.
I said, “I’m good, sir. I appreciate it, thank you.”
He said, “You want to get a picture?”
I said, “Do a cow produce milk?”
We all laughed.
So all of us took a picture together. Then Brittney got her picture, her mom got hers, and then we started the party.
Let me tell you something — there were kids at that party whose families are some of the richest in the world. I felt so poor, lol.
During intermission, when they were showing videos of everyone saying “Happy Birthday Sasha,” Mr. Obama was standing on the side of the stage. So I went and got a drink. He looked at me and said, “What are you drinking?”
I said, “A vodka cranberry. What you drinking, sir?”
“A dirty martini — that’s how I roll.”
We laughed.
After the videos were over, the first song I played was “Shining” by Beyoncé — Mrs. Obama’s favorite song. So you know they were all on the dance floor.
And somewhere… somewhere…
There’s a video. 🤭🤫🤐🥳
That was one for the books 🥳🥳
