The president was joined by Jay-Z and Beyoncé at the 40/40 club and attended a ritzy reception at the Waldorf Astoria hotel, but first he headed to a taping of the "Late Show with David Letterman" — where he joked about Clint Eastwood's ill-fated conversation with an empty chair at the Republic National Convention and raved about the White House's very own craft beer.
The friendly banter kicked off with a compliment from Letterman.
"You look sharp," Letterman said as he greeted Obama, who entered the studio to "Hail to the Chief" dressed in a black suit and blue tie. Obama tried to return the compliment — but Letterman stopped him.
"You haven't seen me naked," he said.
"We're going to keep it that way," Obama replied, to laughs.
The banter continued as Letterman pulled out a stuffed, orange cat, which he said his young son had asked him to give to the president. But when Obama tried to place the cat in the empty chair next to him, Letterman stopped him.
Don't you want to "say something to the empty chair?" Letterman ribbed — a clear reference to Eastwood's odd appearance at the RNC, which included a dramatic speech directed at an empty chair.
Reflecting on his own convention, Obama said that it was "terrific — except people always realize how much better Michelle was than me."
The president's appearance on Letterman's show delighted supporters who got tickets without realizing Obama would be a guest.
"It's like, 'Oh my God! Obama!'" said Angela Polo, who was celebrating her 35th birthday, before the taping.
"It feels a little unreal," she added. "I think it'll be funny. I think Obama's a great speaker and he has a great sense of humor so I think we'll be in for a great show."
About 500 ticketholders lined up outside the Ed Sullivan Theater at Broadway and 53rd Street for the Letterman taping, as barricades blocked off surrounding streets and sidewalks. Staff on the show said the Secret Service had been preparing for the president's visit all week.
"I didn't know [Obama would be appearing on Letterman] until I walked up here and I saw this long line and cops everywhere," said Woodworth Mataele, who was waiting in line to see the show.
"I'm originally from Hawaii, so of course he has a huge following in Hawaii," Mataele added, referring to Obama's childhood home. "I think both parties are very extreme currently. I'm just looking to see if there's any moderate conversation."
Crowds began cheering loudly as the president's motorcade rolled up Broadway, through Times Square, shortly before 4:30 p.m., flanked by police motorcycles and squad cars. Many fans snapped cellphone photos, while others waved.
The president was the only scheduled guest on Letterman Tuesday night — which marked his second appearance on the show.
Obama also talked about the White House's latest unconventional venture: brewing its own beer. Obama admitted that he didn't know whether or not it was actually legal to brew at 1600 Pennsylvania Avenue, but joked that, "If the presidency thing doesn't work out, I got a little micro-brewery thing going on.... This is tasty beer."
Obama also addressed several more serious topics, including the video of Romney released this week, in which he's seen telling millionaire donors that 47 percent of Americans don't pay taxes and "believe that they are victims" who are "entitled to health care, to food, to housing, to you-name-it."
"One of the things I've learned as president is you represent the entire country," Obama told Letterman in response, slamming Romney for his decisive remarks.
"If you want to be president, you have to work for everyone," he said.
After the taping, the president headed to a ritzy reception at the Waldorf, where he made his reelection pitch to about 200 people, who paid at least $12,500 per family to attend, his campaign said.
During his remarks, Obama joked that Jay-Z "now knows what my life is like."
"We both have daughters, and our wives are more popular than we are," he told the crowd of about 100 people, who paid $40,000 each to attend. "It’s hard, but it’s okay."
He also compared his upbringing to "Jay and B"'s, saying that all three shared similar life stories.
"We remember what it's like not having anything, and we know people just as talented as us that didn't get the same break, the same chance," he told the audience, stressing the need to pass that good fortune onto others.
"We don't slam the door behind us," he said. "We prop it open."
With pool reports