The World's Most Righteous Assholes

Jeffrey Ross is famous for, among other things, posing this question to Courtney Love and a viewing audience of millions in 2005: "How is it possible that Courtney Love looks worse than Kurt Cobain?"

Ralphie May is famous for, among other things, making fun of retarded people's inability to pronounce the phrase mentally challenged Americans: "Shit! They can't say they're mentally challenged Americans! Because they're 'tards!"

Catch people behaving in these deeply antisocial ways at, say, Denny's, and you'll figure a fight is brewing. But Ross and May are amusing when they skirt the bounds of propriety. And laughter has a way of making ugly things palatable, or even enjoyable, which is why their propensity for nasty statements has earned Ross and May coheadlining status Thursday night at the South Beach Comedy Festival, where they're being billed as "The Meanest Men in Comedy."

Jeffrey Ross is widely known as the "Roast Master General" from Comedy Central's celebrity roasts. He is breathtakingly vicious at these events — for example, within a minute of making the Cobain joke, he said, "I wouldn't fuck Bea Arthur's dick with Andy Dick's pussy," while both Arthur and Dick looked on — and his reputation has preceded him here. Yet I am fairly certain Ross is the sweetest man I've ever interviewed.

While talking, he brushes over the "nasty" aspect of his career — "every comic needs a hook," he says — and with little prompting, spends most of the time discussing his work abroad with the USO. He turned his forays in Iraq into a camcorder-shot indie called Patriot Act: A Jeffrey Ross Home Movie, which was released in 2005 to friendly reviews. That he still talks so eagerly about it two years later is good evidence that the experience meant more to him than an opportunity to grandstand on film. Asked how much time he has spent with the troops, he says he doesn't know. "I've been to Iraq twice; I've been to Afghanistan once; I've been down to Guantánamo; I've been down to [New Orleans after Hurricane] Katrina; I've been to the hospitals in Washington; I've been to Kosovo, Japan ... Africa, Alaska, Hawaii — so I'm afraid to add it all up, honestly. 'Have jokes will travel,' as Bob Hope used to say."

The first time Ross went to Iraq, he did so largely unwillingly; he got drunk and was guilted into the adventure by Drew Carey. "When I went back," he says, "I went back for more of the right reasons. It felt like on subsequent tours I was giving a huge morale boost to myself and my life. Honestly, I've gotta tell you, they're the greatest crowds in the world — so, selfishly, I love the shows. You think about people who need it the most, folks who really need a laugh; you think about soldiers in combat wearing a bullet-proof vest. When a joke penetrates that bullet-proof vest, there's no greater feeling for a comedian. I don't think I really understood the job description of being a comedian until I did my first USO tour."

Ross enjoys telling a number of amusing, or at least bizarre, stories about his time in Iraq's Sunni Triangle — celebrating Rosh Hashanah in Saddam Hussein's Birthday Palace with Jewish-American soldiers is a notably weird experience for a Jewish boy from Newark — but pauses delicately over the more poignant ones. He wants to explain himself perfectly, and seems uncertain of his ability to do so without ready-made references to, say, Pamela Anderson's vagina.

"There were soldiers in the audience, and I was looking at them. They looked just sort of tired and sad. They'd come in late, and I asked their commanding officer why they looked tired and sad and weren't having a good time. They'd just come from a memorial service for a guy that died yesterday. I said, 'What're they doing at the comedy show?' He said, 'I ordered them to be here.' And over the course of the show — I'm not saying they had a party, but they broke into some smiles. Sometimes that's all you can really ask for."

Ralphie May has been to Iraq, too, though he doesn't talk about it much. What May likes to talk about is his young daughter — April June May — and race. On the latter subject, he gets away with a lot — so much so that the white comic once hosted the Big Black Comedy Show. "To be perfectly honest," he says, discussing his imminent trip to South Florida, "I like the Cubans. I don't like Cuban men, because they try to fuck my wife in front of me. They're filthy animals that way. I mean, they'll hit on a bride walking down the aisle. They're dogs." Hearing this, I wonder where it is that he likes to go when he's in Florida. The rejoinder: "Anywhere there's a Cuban!"