In 2014, Jeffrey Epstein wanted a bunch of comedians to join him for dinner at an Italian restaurant on the Upper East Side.
Chris Rock was high on his list. David Brenner, the stand-up comic and frequent Johnny Carson guest host, was a probably, then a yes, then ultimately a no — he was under the weather. Lewis Black was not to be invited: It seemed Epstein had not found the comedian that funny when he had come over a year earlier. Finally, Rock was a no as well. As it turned out he had plans with his daughter.
“Now the pressure is on me,” the veteran comic Bobby Slayton emailed Epstein ahead of the dinner, “to carry ALL the ‘funny.’”
“Unless,” Slayton added, “Woody decides to chip in.”
Woody Allen was Epstein’s friend and his ace in the hole — a luminary who, like Leon Black in finance and Bill Gates in tech, could draw others into Epstein’s orbit. A generation of younger comics worshiped Allen, the Oscar-winning director, screenwriter and humorist.
Planning for the gathering is detailed in the thousands of emails collected amid a sex-trafficking investigation into Epstein and released recently by the Justice Department.
It was one of several of what Slayton called “our legendary dinners” — occasions that Epstein hosted at which funny people were implicitly expected to sing for their suppers. According to the contemporaneous emails and subsequent accounts, comedians met with Epstein roughly a half-dozen times, typically at his Manhattan townhouse, where they enjoyed fine wine and funny conversation.
None of the comedians have been accused of any wrongdoing in relation to Epstein, and nothing in the emails suggests that meeting women was part of the rationale for the gatherings.
Epstein was an earnest fan of comedy who attended shows in Manhattan, Palm Beach and Montreal and traded jokes over email with associates. He viewed humor as a marker of intelligence, Jackie Martling, the comic, recounted on a podcast last year.
“Anybody that’s really smart loves jokes,” Martling quoted Epstein as telling him over a meal, “because they’re little problems, and the way they work themselves out.”
But details of these occasions also illustrate how Epstein was able to shroud his record as a sex offender by assiduously cultivating titans of government, finance, the academy and, yes, comedy, whose very presence at his dinner table appeared to enhance his respectability.
The gatherings recounted in the emails occurred after 2008, when Epstein pleaded guilty to soliciting prostitution from a minor. At the time of his death by suicide in 2019, he was in prison facing federal charges of sex trafficking minors in Florida and New York between 2002 and 2005.
Epstein’s attitude toward comedians can seem queasily familiar. He proffered perks, including fancy dinners and free stays in his mansion’s many apartments, while restlessly drawing comedians into what he hoped to be an expanding circle. Slayton, who did not respond to a request for comment, appeared to stay at the apartment occasionally and referred to it in emails to an Epstein assistant as “Chez Slay.”
Epstein sought to leverage one set of friendships with comedians to add more, sometimes reaching out the day after hosting a comic to ask if he might invite the comic again.
Following one dinner in 2015, Epstein emailed the comedian Nick Di Paolo: “Thanks for coming last night,” adding, “If ok with you I will contact you on my return to New York.”
Di Paolo’s reply suggested that, for all of Epstein’s efforts, people often were conscious of his criminal convictions.
“Give me a little time to process that last part,” Di Paolo wrote, referring to Epstein’s enticement of continued friendship. “As you know you are a bit of a controversial guy. I mean no offense by that at all. Lol.”
The emails do not contain any discussion of why Di Paolo accepted the initial invitation.
(Di Paolo did not reply to requests for comment. Neither did Rock, Allen, Lewis Black or Martling.)
Last year Allen told the British newspaper The Sunday Times that Epstein was a “substantial character” whose dinners had been filled with “illustrious people” who were “fun to listen to.” But he said that he had never noticed Epstein with underage girls and that Epstein had told him he was a victim of false imprisonment.
“He told us he’d been in jail,” Allen said in the interview, “and that he had been — I can’t remember the word — but that he’d been falsely put in jail in some way.”
Lewis Black, Slayton and Martling have said in interviews that they never saw Epstein hanging out with underage girls. Slayton told a Daily Beast reporter that he felt obliged to visit some with Epstein as a way to “pay respect” for the free lodging he had been offered.
Confirming Allen’s availability appeared often to be Epstein’s first step in planning a dinner with comedians.
Even Di Paolo, before brushing Epstein off, mentioned: “It was a real kick meeting you and Woody!”
Allen and his wife, Soon-Yi Previn, were listed as guests at several of the dinners and Allen was at times deferred to.
When an assistant of Epstein’s asked Previn and Allen to dinner, she once asked if they would mind whether Rock were invited (“of course no problem,” Previn responded). Another time, Epstein confirmed with Previn that he should not invite Howard Stern because Allen disliked the radio host. Previn answered in the affirmative, describing Stern as “a mortal enemy” and saying that Allen felt he had sided with Mia Farrow, Allen’s ex-partner, when their relationship fell apart. (It ended after Allen began a relationship with Previn, who is Farrow’s adopted daughter.)
Epstein and Allen also traded complaints about the treatment of Bill Cosby, the comedian who was accused of sexual assault.
“Cosby is being persecuted. Ok, even if he’s guilty no one died,” Allen wrote. Epstein responded: “Cosby unable to catch a break.”
One reliable link to comedians for Epstein was Slayton, the veteran humorist and actor billed as “the Pitbull of Comedy.”
Several times, Epstein asked Slayton to help put together a gathering — “can we do a dinner when you are in ny” — and Slayton would oblige: “Let me call the ‘Boys’ and see their story.”
Slayton recalled on a 2024 podcast that their relationship began years before when Slayton’s manager routed him a request from Ghislaine Maxwell, Epstein’s longtime companion, to perform stand-up at a private party for Epstein in exchange for travel and a room. Slayton declined the gig but Epstein later came to see him perform in Palm Beach, kindling their friendship.
In a 2016 email to Allen, Epstein asked whether Slayton might appear in one of his films. Allen replied: “Maybe Bobby could do a small bit in the Amazon movie.” Slayton has credits in Allen’s “Wonder Wheel” (2017) and “Rifkin’s Festival” (2020).
Epstein also reached out to Slayton via email shortly after Slayton’s wife died to see how he was doing.
In a podcast appearance two years ago, Lewis Black recalled attending an Epstein dinner in early 2013 alongside Allen, Brenner and Dick Cavett.
He described it as “wild” and recalled seeing “young girls flitting about,” without going into more detail. The magician David Blaine showed up and performed tricks for the group, he said. (Blaine did not reply to a request for comment.)
Still, as Black recounted it, there were reminders that Epstein’s networking was not always fun and games.
Epstein drew the group’s attention to a whiteboard with writing on it at one point, Black said, telling his guests that the markings had been made the night before by Israel’s defense minister as he described a weapons system Israel would use in case of attack.
Jason Zinoman contributed reporting. Alain Delaquérière contributed research.
Marc Tracy is a Times reporter covering arts and culture. He is based in New York.
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