July 15th, 2009 – a day that shall live in comedic infamy. The Obama administration’s first direct hit from reliably friendly allies. Former Saturday Night Live star, now stand up comic Dana Carvey was the guest on the new Tonight Show with Conan O’Brien. When O’Brien asked Carvey his opinion of Obama, Carvey trotted out some fresh material. “I’m worried. The economy just had a heart attack, but Barack just wants to work on the knee,” Carvey riffed. “Should we do CPR? No, we’re gonna fix this knee. We can do CPR when it’s efficient and cost effective, but right now we’re going to work on the meniscus. “Carvey concluded the bit suggesting George W. Bush would have used an economic “crash cart.” “Tax cuts for everybody – CLEAR!” The audience roared. Were they laughing at Carvey’s “dumb guy” Bush impression, or was it the excitement of more money in their pockets as an economic remedy? No matter the audience response. Carvey saw fit to address economic policy in his comedy. That’s telling.

At the same hour, on the same day – The Daily Show’s Jon Stewart opened fire. “Last night, Obama threw out the first pitch at the All Star game. He even played short-stop for a time,” Stewart said. “There’s nothing he can’t do…except create jobs.” Ouch. The audience laughed tepidly. It was as though they couldn’t believe what they’d heard, and Stewart moved past the line quickly.

During the same show, Stewart went on to skewer the healthcare reform fight in Washington. Initially mocking Republicans for sounding the alarm on Obama’s ultimate desire for a “single payer” system, the joke took an unexpected turn. “…that’s just a Republican scare tactic. The Democrats are not proposing a government takeover of health insurance. And they’re certainly not trying to “Trojan horse” us into some European or Canadian-style single payer system,” said Stewart. With that, Stewart played some grainy campaign video from 2008 in which Obama told a cheering crowd, “I happen to be a proponent of single-payer health care.” The next shot is a dumbfounded Stewart back at the desk as he coldly confessed, “Wow. That Communist sounded a lot like our President.”

Since this watershed event in comedy, the Daily Show has taken on a new tone. A day after President Obama declared Cambridge cops “acted stupidly” in the arrest of his friend “Skip” Gates, Stewart took it head on. “Now, I wasn’t at the press conference last night, and I don’t have all the facts. But I think it’s fair to say that Obama handled that question…oh, what’s the word I’m looking for? Stupidly?”

In another segment of the same show, Stewart playfully cheered as Nancy Pelosi and President Obama suggested increased taxes on the wealthiest Americans to pay for health care reform. He pretended to be surprised when he was “informed” in his earpiece that he, in fact was wealthy. “Oh, so they’re coming for me…ok,” Stewart said sheepishly. Remember, Stewarts’s a New York-based millionaire. Theirs is the highest taxation in the country, and President Obama and New York want more from him. Is Stewart sensitive to that? Again, economics and federal budgets as punch lines? You’ve got your answer.

Last week’s Daily Show also featured a montage of the President refuting criticisms of his health care plan. After the string of presidential rebuttals Stewart concluded, “You know a sales pitch is in trouble when it starts with “Look, you’ve got to trust me. We’re not going to kill your grandparents.”

The impression shouldn’t be left that comedy’s liberal leanings are absent. The bias for this president is still deeply entrenched in comedy writers. But writers and performers are also wealthy, privately insured, and often well educated. They have lost much of their own wealth in the markets while beginning to realize the finest doctors and insurers who serve them are growing nervous. Comedians have families and friends in medicine, finance, and industry. Reality is setting in.

The truth of the nation’s growing pessimism and skepticism in Washington is at historic highs and on display every day. Comedians’ choice is clear. Continue to cheer and cover for a president in whom they emotionally invested so much. Or realize the investment just didn’t pay off as they’d hoped and get back to the honesty in their craft.

Never have there been so few jokes directed at a President who deserves so many.

Jon Stewart was just voted “America’s most trusted” by the online readers at Time Magazine after Walter Cronkite passed away. He led the likes of Couric, Williams, and Gibson – all network news anchors who “play it straight.” Meanwhile, Gallup polling reports Obama’s job approval among likely voters age 18 to 29 and 30 to 49 has dropped 6 percent in the last month.

Obama is losing Jon Stewart. The question is: Can Obama get him back?