March 20, 2025

Lil Wayne Chats Up Katie Couric About Retirement

Lil Wayne has a special relationship with Katie Couric. Back in 2009, the pair hung out, bowled
 and talked about what it means to be a gangsta.

The unlikely friendship continued on Monday (September 9), when Wayne (who Couric called “hip-hop’s mad genius”) sat down with the former network news anchor on her syndicated “Katie” talk show to discuss why he dropped out of high school, his dangerous addiction to syrup and why he’s really, really ready to call it a day on his rap career.

Since their last talk, Wayne did a stretch in prison on gun possession charge, so naturally Couric was curious how the other prisoners treated the rapper. “It’s jail,” he answered when asked if the other convicts were excited to see such a famous face. “So, for the first 20-30 seconds you’re like, ‘Oh my God that’s really him,’ then … the reality of where you’re at clicks right back in.”

Couric, or (“Miss Katie” as Wayne referred to her the first time around), also asked about how Weezy’s children are doing, which caused the Young Money boss to shake his head a blush a bit. “My oldest is my beautiful daughter she’s 14, Reginae. She’s awesome, she’s a firecracker,” said Wayne, who dressed conservatively in a white t-shirt, khakis and a “trippy” baseball hat. “Personality out of this world.” He called his three sons his “everything” and reiterated that he wants to retire in five years when he turns 35.

“Whatever they want to do,” he said about his plans to spend time with them when he hangs up the mic. “I don’t want to have no influence … ‘Hey you must do this, you must do that.’ Because I didn’t have that and because I didn’t have that I grew up to be exactly what I wanted to be and how I wanted to be. I want that for all of my kids … I know I’ll be ready to retire at 35 because I am so ready to retire now!”

The admittedly “odd couple” shared a laugh over the “I’m a gangsta Miss Katie” line that Wayne dropped the first time around, which brought a smile to Couric’s face on the first show of her second season.

Asked if he regretted not finishing high school, Wayne, an honor student, drew a laugh from the studio audience when he said, “Not at all … I mean, kids, please finish high school. And all my kids, you are finishing high school!” Getting serious, Weezy explained that it was actually his mother’s idea for him to drop out.

At the time he quit, Wayne already had a platinum album out and one day when she saw him getting ready to go to his public high school, his mother saw him getting ready for the day, which included packing his gun in his backpack. “You gotta bring that to school with you?” she asked him. “You don’t want me to bring it?” replied. “I do,” she responded after thinking about the weapon she’d bought him for protection.\

Worried that he had to go to school armed, she counseled him to get his GED and then go to college instead.

Admitting that he’s an “excessive” person who tends to do things to the extreme, Wayne also opened up about his abuse of syrup. Doctors thought the series of seizures
 he suffered earlier this year were a result of dehydration, lack of sleep, working too hard and what they thought was newly-discovered epilepsy. Wayne’s mother, however, revealed that when he was younger he “fainted” at a public park, which she now realizes might have been a seizure.

While looking for a source of the seizures, Wayne told his physicians that he’d cut way back on syrup, but that he’d been taking pain pills that also had codeine in them.

Asked if he’s still sipping, Wayne said, “No I can’t.” And when Couric wondered what made him stop, he said, “My doctors. I was doing it too much.” While his doctors couldn’t tell him what to do, they suspected his mother could have an influence on his drug abuse issues. “I suggest that your mom tell you to stop,” Weezy said the doctors told him, after discovering that one of his cousins had epilepsy and that another had died of the disorder.

And, sure enough, the rapper’s mother did tell him to cut it out and he, of course, listened.

In addition to giving the Trukfit boss his own custom “Katie” branded skateboard, Couric also had her 2005 minivan pimped in Wayne’s honor for the show. “You got sheepskin!” Wayne laughed when he heard about the interior of the car she’s giving away to one of his fans.

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