Shaquille O’Neal has rubbed shoulders with some of the biggest names in the world. From Hollywood elites to music icons, his celebrity encounters are endless. But when it comes to his sons, they’ve had their fair share of hilarious and cringeworthy moments, too. Just last month, Shaq’s son, Shaqir, had fans doing a double take when he posted what seemed like a cozy moment with Beyoncé—only for everyone to realize he was hugging her wax figure. And let’s not forget Shaq himself, who took things to another level by using AI to craft his own love story with Marilyn Monroe.

However, this time, his 24-year-old son isn’t dealing with a crush—he’s reliving a 22-year-old moment that’s as awkward as it gets. And, of course, it involves another A-list star—Jessica Simpson, the $200 million American singer.

The moment in question dates back to 2003, when Shaquille O’Neal hosted Shaqtacular, a charity event under AEFK (Athletes & Entertainers For Kids). The fundraiser aimed to uplift underprivileged children. During the event, Jessica Simpson took the stage alongside Shaq and his sons, Shareef and Myles. But what stole the show years later was an old picture that resurfaced on Shaqir’s Instagram.

In the snapshot, Jessica beamed with excitement, while young Shareef looked down at his nails, seemingly unimpressed by the pop sensation standing next to him. Shareef couldn’t help but laugh at the resurfaced image. He reshared it on his IG story, writing, “I am still here.”

Speaking of celebrity crushes, Shareef O’Neal once had his eyes set on Rihanna. Back in 2023, he took to Instagram to make his feelings for Rihanna clear, posting a photo with the caption, “waiting for Rihanna like…” But Shaq, always ready to steal the spotlight, wasn’t about to let his son have this one. he jumped in to crush Shareef’s dreams. “She don’t want you, she want me, I am sexier,” he declared, leaving fans cracking up at the father-son showdown. Yet, if anyone thought Shareef would just take the L, they clearly underestimated him. He fired back with a bold claim: “I already bagged her, it’s too late man.” 

Shareef’s ‘too cool’ moment with Jessica Simpson? It’s just another chapter in the O’Neal family’s ongoing saga of hilarious and sometimes head-scratching celebrity encounters. It’s like they’ve got a knack for finding themselves in these situations that are just…memorable. And honestly, it’s not just Shareef. The whole family seems to have a talent for creating these viral moments, whether they mean to or not.

Shaquille O’Neal and son’s weird valentine

This year, the O’Neals found their perfect valentines—sort of. Shaqir, the youngest of the bunch, took to Instagram to share his “romantic” moment. The 21-year-old posted a picture of himself embracing none other than pop icon Beyoncé. Keeping it simple, he captioned it, “Happy V-Day y’all,” before sneaking in a playful “miss u 🐝.”

But as much as Shaqir might have wanted to fool his followers, a closer look revealed the truth—he was actually hugging a wax-like statue of Queen Bey. And funny enough, this wasn’t even his first time pulling this off. Shaqir had already posted the exact same picture not once but twice—on “National GF Day” in 2023 and even way back in 2019 on Beyoncé’s birthday. But Shaq took things to another level.

For Valentine’s Day 2025, the Big Diesel turned to AI. He created an entire love story featuring none other than Marilyn Monroe. The hilarious clip opens with Shaq chatting with Monroe over the phone, setting the stage for a whirlwind romance. And because Shaq never does things halfway, the video takes it to extremes—there’s a wedding, a whole relationship arc, and even a kid.

And while fans found it hilarious, Shaq’s kids weren’t as entertained. His daughter Taahirah made her feelings clear with a simple ‘fed up’ face GIF, while Shareef had the best reaction: “bro what.”

So one thing’s for sure—the O’Neal boys know how to keep the internet talking.