First appearance of Obama Quest.

Jon Stewart: Let me ask you a serious question, when you woke up this morning, did you feel a little colder, a little sadder, a little lonelier... a little less hopeful? There's a reason for that.
CNN Anchor: Barack Obama has left the country.
Jon Stewart: (gasping) Don't take our hope away! We miss you.

Jon Stewart: Now certainly it's not uncommon for Senators to make this kind of mission trip, but Obama's trip is getting more attention than usual. Tagging along are not 1, not 2, but 3 major network news anchors!
Jon Stewart: Now, as I understand it, on every night of the trip, Barack Obama will give a rose to every anchor he wants to stay. The ones that don't get a rose have to go home.

Jon Stewart: Come on, this guy (Obama)'s a newbie! You can't snag one faux pa, a misstep, a boo-boo, a brain fart? Something small! A geography mix-up!
(Switch to Clip)
John McCain (July 21, 2008): It's a hard struggle. Especially given the situation on the Iraq-Pakistan Border.
Jon Stewart: "The Iraq-Pakistan Border", Also known as... Iran.

Hercules

During the Obama Quest animation, we see Obama fighting a hydra and a cyclops- things that the mythological character Hercules is famous for doing.