Thanks, Obama: My Hopey, Changey White House Years

That’s right, buddy. Look who’s still here.

It was only at the very end of the meeting, as we rose from the surprisingly comfy couches, that Favs brought up the Alfalfa dinner. The right-wing radio host Laura Ingraham had been in the audience, and she was struck by the president’s poise. “She was talking about it this morning,” Favs told POTUS. “She said, ‘I don’t know if Mitt Romney can beat him.’”

By this point, President Obama was showing us the door. But when he heard Favs’s story he paused briefly and puffed up. It was like watching a boxer at a weigh-in.

“Well,” he said, “Mitt Romney can’t beat me.”

If chest bumping had been permitted in the Oval, we would have gone for it. Instead we did the next best thing, laughing with outsize confidence as we strutted from the room.

The incident left me with no grand illusions regarding comedy. I didn’t think a few one-liners could create new jobs or push our approval above 50 percent. Still, I was proud. Without violating the ban on political activity, I had helped POTUS send a warning shot across Romney’s bow. Maybe I even discouraged an anti-Obama SuperPAC. The point was that I had played some small role in the biggest political battle of my lifetime. And I hoped that when the 2012 Correspondents’ Dinner rolled around, I’d have the chance to do it again.

WHEN I WORKED AT THE WHITE HOUSE, PEOPLE OFTEN ASKED ME IF I used jokes to advance the president’s agenda. I always said no, by which I always meant yes. That’s not to say each punch line was poll tested. I simply felt that if the leader of the free world was required to host a comedy night, it ought to be worth his time.

Under Jon Lovett’s supervision the previous year, POTUS’s assault on Trump had more than met this standard. The conventional wisdom, which I wholeheartedly subscribed to, was that Obama had “destroyed” the birther king. He had “demolished” him. But in late 2011, Lovett moved to Hollywood to write sitcoms. I became, by default, the White House’s token funny person. As I prepared to run the joke-writing process for the first time, destroying and demolishing Romney seemed like obvious goals.

This was easier said than done. Back in 2011, Trump was the rare breed of public figure loathed by Democrats and Republicans alike. Romney was different. He had friends. Step even an inch over the line, and they would complain to reporters, who would milk the ensuing controversy for days.

With a frontal assault out of the question, the best we could hope for was a series of bank shots. By laughing at his own expense, POTUS could appear both confident and humble. By injecting arguments directly into setups and punch lines, he could bypass the media back-and-forth. Perhaps most important, by joking about controversy, he could diffuse it. If the president’s willing to laugh at something, how bad can it really be?

By the time I began writing jokes, three weeks before the dinner, there was plenty of controversy to diffuse. In March, a hot mic caught POTUS telling Russian president Dmitry Medvedev he’d have “flexibility” after the election. Policy-wise, this was reasonable. Stripped from context, with the frisson of excitement that comes from eavesdropping on world leaders, it looked bad.

So did the debacle unfolding at the Government Services Administration. The agency’s sole purpose was to spend taxpayer money wisely. Yet it had recently shelled out more than eight hundred thousand dollars for a Las Vegas conference featuring a mind reader and a clown. And GSA staff weren’t the only federal employees whose entertainment choices had gotten them in trouble. On a recent trip to Colombia, several Secret Service agents had been caught soliciting prostitutes when one of them skipped out on the bill.

Then there were the scandals involving dogs. I know that sounds absurd. It is absurd. But the fact remains: in April 2012, two canine controversies were major political news.

The first dated back to 1983, when a young Mitt Romney drove his family to a vacation home in Canada. This was unremarkable. What was remarkable is that, the car overstuffed with bags and children, he had transported his family’s Irish setter in a carrier strapped to the roof. Hoping to contain the fallout, Romneyites dug up a scandalous story of their own. In his autobiography Obama admitted that, as a six-year-old in Indonesia, he had eaten dog meat.

The whole thing was stupid. Neither anecdote said much about the president each man would make. Yet political commentators couldn’t get enough of these stories. Was it worse to mistreat a dog as an adult or ingest one as a child? In 2012, somewhat astonishingly, plenty of political reporters felt this question was worthy of their time. And it was my mission to leave no controversy, real or nonsensical, unaddressed.

To that end, I compiled a long list of topics and sent them out to what amounted to our writers’ room. David Axelrod and Jon Lovett sent in jokes from the growing Obama diaspora. Other one-liners came from Jeff Nussbaum and his West Wing Writers team. More than a half dozen contributors came from entertainment rather than politics. Nell Scovell created Sabrina the Teenage Witch. Kevin Bleyer was a producer on The Daily Show. Nina Pedrad wrote for 30 Rock and New Girl. Judd Apatow was (and is) the leading comedy mogul of his generation, behind everything from Girls to Knocked Up to Freaks and Geeks.

Perhaps our friends in Hollywood knew how to crank out an endless series of amazing jokes. I certainly didn’t. For me, the secret to writing one funny line was to write about twenty-five awful ones first. Most evenings I would comb through the day’s rubble and sigh. But after picking the diamonds from the rough, and combining them with material coming from outside the building, a monologue began to take shape.

A few days before the dinner, Favs and I went to the Oval to present about forty of our favorite lines. Together with David Plouffe, the president’s senior advisor, and Jay Carney, the press secretary, we sat on the couches while POTUS read out loud. Each time he laughed, I made a mental note. Each time he didn’t, I had a mental breakdown.

Then he reached my first dog joke and my heart stopped beating entirely. It relied on an obscure reference to one of Sarah Palin’s lines from the 2008 campaign. It also involved eating man’s best friend. As POTUS read off the page, I wondered if we hadn’t made a mistake putting it before him.

“Sarah Palin’s getting back in the game, guest hosting on the Today show. Which reminds me of an old saying: What’s the difference between a hockey mom and a pit bull?”

He paused, just slightly.

“A pit bull is delicious.”

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