How Funny Is Obama?

On Saturday night the president tried out his best shtick in front of Sarah Palin, Warren Buffett, and 400 others. Sandra McElwaine on Washington's most exclusive night of comedy.

01.30.09 6:38 AM ET

In Washington, a town known for bloviation rather than whimsy or wit, the wacky season is just about to begin. It kicked off Saturday night when newly minted President Barack Obama made his debut at the venerable Alfalfa Club, as the star of its annual dinner. Founded in 1913 by four Southern gentlemen, who, for some unknown reason, decided to celebrate the birthday of General Robert E. Lee, the Alfalfa Club’s annual dinner is the most prestigious of the city’s innumerable comedic events. (The club itself consists of 200 members who endeavor to emulate the tone of good cheer and good fellowship established by the original all-male enclave. The first women—Elizabeth Dole, Katharine Graham, and Sandra Day O’Connor—were only admitted in 1994.)

Sandra Day O’Connor drew a standing ovation when she came up with the following: “We have a majority of the Supreme Court here tonight…What do you say, guys, just for fun, we overturn Bush v. Gore?"

The Alfalfa Club dinner is part of a series of high-wattage events including the Gridiron, the Washington White House Correspondents dinner, and the Radio and Television Correspondents Association dinner; but it is the most sought-after ticket of the season because it gives members an audience with a collection of super power brokers including Joe Biden, Michael Bloomberg, Vernon Jordan, and 400 other guests—members of the Cabinet and Supreme Court, major politicians past and present, the Joint Chiefs of Staff plus what remains of the Masters of the Universe—to schmooze with each other and exchange a handshake, or wave, with the president and first lady, who almost always attend. Wannabes were still clawing on Saturday for invites to meet the Obamas that night.

Although the list is never revealed until the night of the party, this year Sarah Palin was on the roster (everyone was buzzing about whom she would sit next to), as were House Speaker Nancy Pelosi, White House Chief of Staff Rahm Emanuel, and Obama chum and adviser Valerie Jarrett. Also on the list: Henry Kravis, Rupert Murdoch, Warren Buffett, and George and Barbara Bush. Hillary Clinton, however, has canceled. “I wonder if there’s a crisis in the Middle East,” questioned one insider.

"We have had five networks wanting to stand in the lobby and cover," reports a member of the dinner committee. "The Hilton is worried about how many will be there. We have never had this much attention on the dinner in advance. I don’t know if it is Obama or Palin."

In Washington, a sense of humor is an oxymoron and being funny is both hard work and a serious business: No politician wants a joke to be DOA. And though topical humor tends to be transitory, a really bad gag can take on a life of its own and curdle a political career.

Enter ghost writer Landon Parvin—the go-to guy for political mirth. The low-key and low-profile Parvin began his career in the Reagan White House by helping the president spoof his theatrical background and laid-back lifestyle. Parvin created headlines when he penned the lyrics for “Second Hand Clothes,” a song Nancy Reagan delivered at the Gridiron dinner of 1982, which made fun of her penchant for designer duds. He is typically perceived as a Republican jokester because he has written for so many members of the GOP, including former Secretary of State Jim Baker, John McCain, and all the Bushes—including Barbara and Laura. In reality, he is an equal-opportunity scribe who, over the years, has created more memorable material for more grand poobahs at more grand dinners than anyone else in Washington. To wit, Parvin has been a member of the Alfalfa Club for 26 years.

“I have to like the person, and agree with their politics,” he confides. “Writing humor is a very personal business. You have to establish a relationship and have a sense of trust. The content should be genial and not too harsh. When things get too partisan it does not work.”

Parvin believes self-deprecation is key.

“Clinton didn’t understand that at the beginning, it took years for him to catch on that making fun of himself was OK…When he did, he was very good at it,” Parvin says. At his last White House correspondents dinner in 2000, Clinton became boffo box office when he said: “A year from now I’ll have to watch someone else give this speech. And I will feel an onset of that rare affliction, unique to former presidents. AGDD—Attention-Getting Deficit Disorder.”

Mark Katz, a Democratic wordsmith, Daily Beast contributor, and head of the Soundbite Institute, a firm that specializes in creative content and "on-message" humor, penned those words. He agrees that the first rule of political humor is "be self-deprecating." The second rule is "repeat as necessary." The third rule is "once you have been sufficiently self-deprecating, you have acquired the right to be self-deprecating on behalf of others."

At the Alfalfa Club, poking fun at oneself is de rigueur. There are no ribald jokes or raunchy asides. No one takes themselves or anyone else seriously, observes longtime member James Symington. “The sole purpose of the entire evening is to get together and have a good time,” he said. Symington recalls George H. W. Bush, also a member, showing up in an elaborate Mandarin costume spouting a Chinese poem when he was US ambassador to China—and after his presidency and original parachute jump, marching on stage resplendent in full flight regalia, dragging his chute behind him.

Presidents George H.W. Bush and George W. Bush and their wives, Barbara and Laura, have always been faithful attendees. In 2007, W. told the audience, “A year ago my approval ratings were in the low 30s, my Supreme Court nominee withdrew, my vice president just shot someone...Those were the good old days!”

When Barbara Bush spoke about her son, she quipped: “I can now see in that little boy some of the presidential qualities he exhibits today...such as his way with words. I’ll never forget the paper he wrote in fourth grade where he explained that in 1519 Ferdinand Magellan set out to circumcise the world.” She brought down the house.

Sandra Day O’Connor drew a standing ovation when she came up with the following: “We have a majority of the Supreme Court here tonight…What do you say, guys, just for fun, we overturn Bush v. Gore?

“It’s true I’m 76 years old. We’ve all heard that women of a certain age are susceptible to mood swings and irrational behavior. We usually hear this from men driving around in convertibles with 22-year-old bimbos.”

“She was really pumped and ready to go. I didn’t expect that,” says Parvin. Crafting humor for supersize egos can be a perilous, high-wire act. You never know what will happen, when a line will have to change, or someone’s wife, at the last moment, will announce, you can’t say that!”

Timing and delivery are also essential. Parvin rehearses each client with a stopwatch carefully, counting the seconds to allow for both pauses and laughter. A good speech should last no more than ten minutes.

He predicted this year’s crop of jokes would focus on Obama’s BlackBerry, Bernie Madoff, and Rod Blagojevich; and that the glossy new president, who exudes sophistication and has an innate sense of grace and style, would shine. (Apparently his speech was being scripted in-house—neither Parvin nor Katz know the content or who is involved.)

“It’s a fresh start and everybody is rooting for him to do well,” says Parvin. “He seems to have a natural instinct and I think he knows that part of being president is that you have to go out and be funny.”

Making ‘em laugh, however, has to be based on a connection to reality. “You can take a kernel of truth, understate, exaggerate it or exhort it, but like a Picasso painting, there’s got to be something real behind it,” notes Parvin.

How to succeed in showbiz in Washington? Washington satirist and Daily Beast columnist Chris Buckley has the answer.

“Hire Landon or Mark, pay them upward of anything they ask, and then add 15 percent.”

Sandra McElwaine has been a reporter for The Washington Star, The Baltimore Sun, a correspondent for CNN and People and Washington editor of Vogue and Cosmopolitan. Currently she writes for The Washington Post, Time and Forbes.