There was a time when the prospect of a sitting President appearing on a late night talk show was considered beneath him. Obama's now made more appearances on Leno than he has for the State of the Union. That all changed in 2009 when President Obama chopped it up with Jay Leno on The Tonight Show set in March of 2009. Obama was fresh on the scene, the gray was there in specs instead of encompassing his entire head and Leno was bout to pass the Tonigh Show torch to Conan.

Four years later, Leno's Tonight Show tenure is back on the clock, but this time Conan's been replaced by Jimmy Fallon. Things have changed for Obama as well. He's not quite as much of a punchline as his predecessors George W. and Bill Clinton, but comedians have found it easier making jokes at Obama's expense in 2013 than they did during his first term.

Controversies within an administration will do that to you. On the plus side, Obama's personal brand remains unfazed, his approval ratings are still high and he has continued making the late night rounds from time-to-time. On Tuesday night, Obama plopped down on Jay Leno's couch for his sixth appearance on The Tonight Show. It was a pleasant exchange, but Leno brought some hard-hitting questions ranging from embassy security to, terror plots, the Robert Snowden saga and how to fix the middle class' woes. Rachel Maddow should be jealous of all the one-on-ones Leno gets with the most powerful man in the world.