Last night was another bit of presidential history for a President who seems to have taken up history making as a hobby. After a rather matter of fact introduction by host Jay Leno, President Barack Obama walked onto the stage of The Tonight Show to the wild applause of the studio audience, and the strains of a more upbeat “Hail to the Chief” by Kevin Eubanks’ Tonight Show Band. Sitting down in the guest chair usually reserved for Hollywood’s glamour set, sports figures and mere mortal politicians, Mr. Obama looked at ease as he traded small talk with the legendary late night host.

Since the announcement that the President would appear on the program, there was tremendous speculation over how he would handle the comedic atmosphere of the show during this time of great economic stress, while not appearing too policy wonkish for the late night set. He quickly showed his humorous side when telling a story about traveling to an event in California and laughing about the manner in which he and First Lady Michelle Obama joke about the excessive security entourage that tracks his every move. One of his best lines of the night was when he compared the political environment inside the Beltway to American Idol where everyone is Simon Cowell.

The appearance was not all fun and games, as Leno did touch upon several hot button issues, including the controversy over the AIG bonuses. Rather than focus on the payouts, the host turned on the prescription that the House of Representatives chose: a 90 percent tax on the individual bonuses. Leno expressed concern over the arbitrary nature of the special tax and wanted to know if Americans should be afraid that Congress could simply impose a tax on people it does not like. It was a delicate question for a President who is still trying to find his way with his Democratic majority in Congress. Mr. Obama spoke in cautious tones but implied that he was not fully on-board with the special tax and said the nation should “stop the horse before it gets out of the barn.”

The President also worked his way around a question by Leno on the performance of Treasury Secretary Timothy Geithner. What began as a question posed by the host on how Geithner was doing on the job took an awkward turn when Leno remarked on Mr. Obama’s framing his answer in a way that sounded like he was offloading the nation’s economic problems to his Cabinet secretary. Leno said as much and, it apparently stunned Mr. Obama but he quickly rebounded with a broad smile, and then proceeded to reinforce that the American public should hold him accountable.

Mr. Obama also provided a Cliff Notes version of the sequence of events that led to the collapse of AIG and was critical of the excesses in the private sector that fueled the economic crisis. At one point in the conversation, the President quipped that the only other place that could get away with such excess is Hollywood. He also spoke openly about the need for some “common sense” regulatory oversight of the financial sector and commented that the real issue is that most of what occurred was actually legal. President Obama contrasted the legalities of questionable transactions with their moral and ethical shortcomings, and the need to change the manner in which business is executed in our country.

One of the best exchanges of the evening was when President Obama sought to explain how the mortgage crisis was fueled by risky behavior in the financial markets and that much of the supposed value the sector was driving was on paper only. He said it was necessary for young people to become engineers, doctors, and teachers, as a way to add real value to the nation. He also said it was incumbent upon Americans of means to sacrifice a little to help support households where children, in particular, may not have access to the necessary resources to succeed. The President did slip toward the end of the interview when he jokingly compared his poor bowling skills with the Special Olympics. After the interview White House aides quickly made clear that the President supports the Special Olympics program and did not mean to offend it by his poor choice of words.

This latest foray by Mr. Obama into unchartered territory for a sitting commander-in-chief is symbolic of a presidency that seems determined to defy conventional wisdom. Where many political observers cautioned that he could damage his credibility by mixing it up with Leno in front of a late night audience, the President clearly relished the opportunity to reinforce that he will not be held captive by the circumstances of the moment. The talk show format allowed Mr. Obama to engage in a “teaching moment” with a studio and television audience in a way that an address to the assembled masses does not provide. There will expectedly be the round of “morning after” armchair quarterbacks ready to analyze everything Mr. Obama uttered on stage. Republicans will surely pounce on the appearance as a sign that the President does not fully grasp the magnitude of the crisis for if Mr. Obama did, the GOP will insist, he would not have wasted time in chitchat with the late night comedian. Such attacks will likely not stick as President Obama uses these “other than Washington” venues to connect with a legion of voters that are purposely disengaged from the mainstream news cycle.