Dick Cheney is ready to laugh about waterboarding.

Conservatives gathered at the Plaza Hotel in Manhattan Monday night to roast the former vice president at an event where many of the biggest laugh lines touched on the most controversial policies of a key architect of his administration’s war on terror. At the gathering, hosted by Commentary, figures including former Defense Secretary Donald Rumsfeld and former Attorney General Michael Mukasey drew a mix of chuckles and winces with jokes that left few lines uncrossed, according to three guests.

Former Sen. Joe Lieberman “said something to the effect that it’s nice that we’re all here at the Plaza instead of in cages after some war crimes trial,” recalled one person who was there.

Other major targets included former Secretary of State Colin Powell, mocked for leaking, and President Barack Obama, who was mocked, repeatedly, for the relative strength of Russian President Vladimir Putin. The event, sponsored by Rupert Murdoch, Paul Singer, and other top conservatives (listed here) also starred Lieberman and Scooter Libby, the Cheney aide convicted of lying to investigators in a leak hunt. Two attendees said the edgy jokes were in appropriate spirit of a roast; the third found them in poor taste, even in that setting. The dinner was, to the surprise of some guests, punctuated by a live performance of Yiddish songs and by an video featuring Cheney’s face on others’ bodies, which emcee and Commentaryeditor John Podhoretz joked he would release only for $1 million in an email to BuzzFeed.

“There were some waterboarding jokes that were really tasteless,” the guest said. “I can see the case for enhanced interrogation techniques after Sept. 11 but I can’t really endorse sitting there drinking wine and fancy dinner at the Plaza laughing uproariously about it.”

Cheney himself told one waterboarding joke, the attendees said, which he attributed to Jay Leno. It centered on a one-shot antelope hunting contest in Wyoming in which the loser had to dance with an Indian squaw. Cheney’s shot got caught in the barrel, producing a dispute over whether it counted as a hit or a miss — and Leno, according to Cheney, joked that Cheney wanted to go catch the animal with his bare hands and waterboard it.

Separately, Rumsfeld joked about Cheney waterboarding fish.

Other jokes touched on Cheney’s having shot a friend in the face; Rumsfeld said one guest recalled that Cheney had “finally showed the world that he actually has a heart” in a book about his health.

Libby, for his part, made light of his imprisonment — and lack of a presidential pardon.

“Libby said George Bush sent a note: ‘Pardon me, I can’t make it,’” one guest recalled.

Libby also joked that Cheney’s dog had urinated in a cabin at Camp David, and that Cheney had sought a pardon — and Bush refused.

A couple people made the point that Vladimir Putin is now running American foreign policy.

It was, said another attendee, “a very sentimental night.”

CORRECTION: An earlier version of this post misattributed the “cage” joke, and mischaracterized the Yiddish songs as “folk” songs. Also, Libby was convicted but never did time. (10/8/13)