Olivia Nuzzi's "Jailbait": An "Outrageous" but "Undeniably Infectious" Song

In a previous post, we related that when Olivia Nuzzi, the former Vanity Fair editor, was an 18-year-old student at Middletown High in New Jersey, she initiated an age-gap affair with 52-year-old Keith Olbermann, the former MSNBC host. Nuzzi was 25 when she began dating her future fiancé, 44-year-old journalist Ryan Lizza, a current CNN analyst. Nuzzi was 30 when she began a “digital affair” with 60-year-old Robert F. Kennedy Jr.. And when Nuzzi was 16, with the stage name Livvy, she recorded “Jailbait".

In the first verse, Nuzzi sang about the undeniable allure of a nymphet, and she shared that she was shameless; however, she warned that an age-gap affair with a 16-year-old could get a man 20 years in jail.

Verse:

Bad things happen when you hear my name

Deny your attraction - but I've got no shame

Sixteen will get you twenty, I've got you locked for life

Don't even think about it, because baby I'm

However, in the pre chorus, she warned men that after being with her, they’ll desire more.

Pre Chorus:

Not your girlfriend

Not the girl next door

Not your girlfriend

I'll give you just enough and leave you wanting more

The 16-year-old sang in the chorus that despite being jailbit, she was irresistible, but warned men that they could look at her but not “play” with her.

Chorus:

Jailbait

I'm jailbait

You try to stay away, but you can't obey

Jailbait

I'm jailbait

You look, but you can't play

Cause I'm jailbait

Ja-ja-ja-ja-jaibait

Ooh, they call me jailbait

In the second verse, Nuzzi sang about the precariousness of “craving sin” (i.e., craving sex with jailbait), which she referred to as an “illegal dream”, and she warned about the potential inability to resist a “teenage queen”.

Verse:

Craving sin, we walk a fine line

A game I win, that word I define

A teenage queen, right in front of you

Illegal dream, killer to pursue

In the bridge, she serenaded that bad things happen to men whom prey upon and “lust criminally” after jailbait, which she, once again, described as an “irresistible” conundrum.

Bridge:

Bad things happen to those who (pray) prey

A basic instinct to die another day

Sixteen will get you twenty, lust criminally

Irresistible, that's why they call me…

In a press release for the “Jailbait”, Nuzzi described the song as: "Offensive", "vapid", "frothy", "bubblegum", "outrageous", "morally bankrupt", and "undeniably infectious". In addition, Nuzzi related that “Jaiilbait” is about “underaged, hyper-sexualized girl[s] in society” whom take semi-nude selfies. Nuzzi wrote that the “sexy” song is about the “obsession with youth and beauty”, which she condoned. And she confessed that she’s the embodiment of jailbait. Nuzzi:

“Jailbait” is about the role of the underaged, hyper-sexualized girl in society. That girl who takes half naked photos of herself in the mirror with her camera phone. It's about pornographic ideals infiltrating our collective consciousness — this obsession with youth and beauty. I'm not saying that any of this is wrong, I'm simply stating that it is. This song is me coming to a societal realization."

And simply put, I am the definition of jailbait.

On her MySpace page, Nuzzi posted that as a 16-year-old singer/songwriter of songs like “Jailbait”, she planned to invade the listener’s consciousness and their worlds. Nuzzi:

Livvy (Olivia Nuzzi) is the future, and Livvy is the past. Preparing to dominate the world and show you the way a pop object lives. Livvy has no off switch, and life is a performance in her eyes. This sixteen year old singer/songwriter plans to invade your consciousness with her killer pop hooks and become the center of your world.

Lastly, Nuzzi’s album was planned to be a “conceptual expansion on "Jailbait", which “explore[d] the good and the bad of this all-consuming porniness”. Porniness?

Famous Age-Gap Relationship: Oliva Nuzzi (18) and Keith Olbermann (52)

Keith Olbermann and Oliva Nuzzi

Ryan Lizza, the CNN analyst and former fiancé of Vanity Fair’s former West Coast editor Olivia Nuzzi, posted “Part 1: How I Found Out” on his Telos News Substack. In the post, Lizza shared that when Nuzzi was a teen, from her “unhappy home in suburban New Jersey”, she randomly “messaged” 52-year-old Keith Olbermann, the former MSNBC host. Consequently, Nuzzi moved into Olbermann’s Manhattan apartment, where they began an age-gap affair. Lizza wrote:

Not that long ago, I had helped her untangle herself from an unusual relationship with Keith Olbermann, the former MSNBC host. She had messaged him out of the blue. They started talking, and soon after, she fled her unhappy home in suburban New Jersey and started living with Keith in Manhattan. 

Rhetorical question: Did Nuzzi initiate the affair with Olbermann because she was looking for a loving (age-gap) relationship, or was she looking for a Sugar Daddy, or both? I ask because Lizza posted that Olbermann paid for Nuzzi to attend Fordham University. (The Lincoln Center campus, I presume.). He dressed her in designer dresses. He draped her in Cartier. And he paid for her luxury West Village apartment. Lizza wrote:

He paid for her to attend college, outfitted her in Tom Ford and Hervé Léger dresses and some $15,000 worth of Cartier jewelry. Later, he covered her rent and furnished her apartment in a doorman building in the West Village. 

There are a number of conflicting reports about exactly when Nuzzi and Olbermann’s age-gap affair began; however, the correct report is that it began when Nuzzi was an 18-year-old high school student at Middletown High. 

Olbermann shared with the New York Times that 18-year-old Nuzzi moved into his apartment in a “Trump building on the Upper East Side”, where they had two Maltese puppies and an “marriage-y” age-gap relationship.

Ginia Bellafante related in the New York Times piece “In This Scandal, the Journalists Are the Story” (Nov. 21, 2025):

Mr. Olbermann had lived with her for a while in a Trump building on the Upper East Side, “if you can believe the irony,” he told me. He said he had discovered her writing on Twitter, where she provided witty political analysis as a student, and he wondered if she might be a good fit for the TV show he had hosted in those days.

They met for dinner. She was 18. He was 52. Instead of working together, they began dating, he said. They got two Maltese puppies and James Thurber-inspired tattoos. “It was marriage-y,” Mr. Olbermann said. “It was very much an at-home-with-the-dogs sort of thing.”

However, a day after their conversation, Olbermann shared with Bellafante that he and Nuzzi didn’t have sex until after Nuzzi turned 19, which is extremely hard to believe. 

It’s worth noting that prior to his relationship with Nuzzi, Olbermann was 47 when he had an age-gap affair with 23-year-old journalist Katy Tur. Nuzzi was 25 when she began dating 44-year-old Lizza. Nuzzi was 30 when she began a “digital affair” with 60-year-old Robert F. Kennedy Jr.. And when Nuzzi was 16, she recorded “Jailbait”, which included the salacious lyrics like: “Bad things happen when you hear my name / Deny your attraction, but I’ve got no shame / Sixteen will get you 20 — I’ve got you locked for life”