Anna Nicole Smith in her younger days was out of this world beautiful, yet somehow always seemed humble, approachable, and kind.
One particular interview from 1995 really shows that side of her—a side many say was later consumed by the industry and people who swallowed her soul.
Joining a very exclusive club
Anna Nicole Smith’s story didn’t start with fame or fortune — she came from humble beginnings in the small Texas town of Media. Life wasn’t easy for her growing up. Her father left when she was just a baby, and she never finished high school.
At that point, no one could have predicted that she’d become one of the most recognizable faces in the world. For a while, it looked like she was on track for the typical path many high school dropouts take — working at a local restaurant, falling in love young, and becoming a mother at just 17.
But Anna had something special — and it wasn’t long before the world took notice. In 1992, after sending in nude photos of herself to Playboy, she landed a coveted spot in Hugh Hefner’s iconic magazine. That same year, she also appeared in ads for the fashion brand Guess, confidently showing off her stunning curves and channeling her idol, Marilyn Monroe.
The following year, Smith hit a major career milestone when she was named Playboy’s Playmate of the Year — joining a very exclusive club of women who earned that title.
With her sexy image, Anna Nicole Smith quickly became a favorite target for celebrity magazines and tabloids. Back then, the bubbly blonde didn’t seem to mind the constant media attention. She once said, “I love the paparazzi. They take pictures, and I just smile away. I’ve always liked attention. I didn’t get very much growing up, and I always wanted to be, you know, noticed.”
By the mid-1990s, she was truly at the peak of her career — landing modeling contracts with some of the biggest fashion brands and scoring a role in Naked Gun 33⅓: The Final Insult, which went on to gross $81 million worldwide.
It’s against this backdrop that Anna Nicole Smith’s memorable interview with Conan O’Brien should be seen.
Many say Conan has never stared into anyone’s eyes as intensely as he did when Anna Nicole Smith was his guest — but the interview also delivered several other unforgettable moments.
Like when Anna Nicole shared a hilarious and embarrassing story from her past. In the interview, she shares a funny yet embarrassing moment that happened during a meeting with film and TV producers.
At one point, her dress came undone, and her breast slipped out.
“I hope he doesn’t get mad at me. I’m not gonna say your name, I promise,” Anna began nervously.
Conan chuckled and replied, “No one watches this show. Don’t worry about it, you know?” — (at the time, the show pulled in around 2.5 million viewers per episode.)
Anna went on: “We were sitting there eating, just talking and stuff, and I had just gotten this new dress. All sitting there talking away, and then my dress came undone — and my boob fell out.”
Anna laughed as she remembered it: “I was laughing so hard, I was so embarrassed — and I had salad in my mouth, so I spit the salad on him!
Trying to escape the awkward moment, she said, “I was like, ‘Oh my God, now I must die,’ trying to get out of this place.”
And of course, Conan just couldn’t hold back.
“I’m sure he wasn’t unhappy. That’s not a bad day at work. Well, that’s not the worst thing that could happen at work — it’s not like having the water cooler fall on your foot!”
“I didn’t call him back for a while,” Anna said.
“Oh really?
“But he did call me—and he even sent me flowers.”
“Oh, that’s nice.”
“So it had a nice ending, which sounds like he’s a nice person.”
“It was very nice.”
Why people praised Conan after this interview
Looking back, a lot of people have praised Conan’s interview with Anna Nicole Smith — and for good reason. Sure, openly commenting on a guest’s sex appeal feels outdated and cringey today, but Conan handled it with way more class than most hosts of the time.
Just imagine how over-the-top someone like Letterman, Stern, or even Fallon would’ve been, one Reddit user pointed out.
Conan, on the other hand, leaned into his usual self-deprecating charm, keeping the tone light, goofy, and respectful. That’s what’s kept him so consistently funny over the years — he never needed to tear others down to get a laugh.
And honestly, thank God this wasn’t one of those clips where the host comes off as a creep. Anna Nicole seemed nervous, and while storytelling may not have been her strongest suit, she came across as sweet and genuine — and that made her all the more endearing.
The most savage joke
Let’s not paint Conan as a total saint, though. While his interview with Anna Nicole Smith was surprisingly respectful, he wasn’t above making jokes at her expense — especially when the headlines got too tempting.
In 1995, when Anna’s 90-year-old husband, oil tycoon J. Howard Marshall, passed away, it was like blood in the water for late-night comedians. The age gap in their marriage had already raised eyebrows, and when he died, the punchlines came fast — and sometimes brutal.
Conan, never one to skip a sharp one-liner, quipped:
“As was his final request, he’ll be buried facedown between two large pillows.”
Jay Leno took the baton and ran with it. He delivered hit after hit:
“She’s taking it pretty hard. She’s not even going to start dating until Friday.”
And again: “She asks that all donations in his name be made in her name.”
David Letterman also got in on the action, offering up this zinger:
“It’s one of those days where I am feeling a little old. This morning I get a call from Anna Nicole Smith. She wants me to send her a copy of my financial statement.”
But if anyone took things too far, it might’ve been Leno again, with arguably the most savage punchline of them all:
“The paper today said she never got to hear her husband’s last words. I guess it was that pillow over his face.”
These jokes may have scored laughs back in the ‘90s, but some say might say they didn’t age well. Especially considering the tragic ending to Anna Nicole Smith’s own life — she died from an accidental drug overdose in February 2007, just months after losing her 20-year-old son Daniel in eerily similar circumstances.
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