Needing to boost his donor base and campaign cash, Obama is banking on elite entertainers for help so often they have essentially become a cast of characters in his campaign. He is using his Hollywood access and raffling it off as a prize to others, tapping into a nation that revels in celebrity even in hard economic times.
Obama's big-name tour makes its next stop on Thursday at Parker's place in the West Village of New York City. The "Sex and the City" star, who is married to fellow actor Matthew Broderick, is hosting a cozy $40,000-per-person fundraiser along with Vogue editor-in-chief Anna Wintour.
While Democrats have long held political and ideological ties to the TV and movie industry, the dynamic is different this time for Obama. His own celebrity has faded a bit after more than three years in the slog of governing, and some reliable donors have gotten so used to seeing him they want more — like a real movie star.
What's more, Obama's team is getting outraised by motivated Republicans in a new, freewheeling environment, one in which wealthy donors can give unlimited amounts of money to outside political groups, known as super PACs, that can have huge sway over the presidential race.
As one counter-response, Obama is borrowing on the power of entertainers to give big bucks themselves and to encourage others to give what they can.
The strategy holds the potential for peril. It allows opponents to paint Obama as hobnobbing for dollars with middle-class angst riding high. The Republican Party lampooned Obama as tone deaf when his campaign promoted the Parker/Wintour event the same day as the news broke of climbing unemployment.
Pressed about Obama's relationship with the stars, his spokesman, Jay Carney, fired back: "Two words. Donald Trump. Next question?" Obama's Republican rival, Mitt Romney, has received fundraising help from Trump, the camera-finding real estate mogul whom Obama has dismissed as a carnival barker.
So far, the rewards of relying on celebrity help have outweighed the risks for the president in a tight re-election race.
"I think people, particularly in times of economic hardship, always look to the entertainment word for a diversion, to take their minds off what's going on in the economy," said California-based Bill Carrick, a veteran Democratic consultant. "I don't think there's much potential here for backlash."
From Tinseltown to Broadway, Obama has surrounded himself with blockbuster names lately: George Clooney, Julia Roberts, Reese Witherspoon, Spike Lee, Will Smith, Oprah Winfrey, Ellen DeGeneres, Cher and many others who make more in one year that most people do in a lifetime.
Obama played basketball with a Batman (Clooney) and a Spiderman (Tobey Maguire), all in one game. He held a private chat in Los Angeles with some of town's young stars last week, from Jessica Alba to Jeremy Renner. He has had some of the most popular musicians in the business perform at his fundraisers, such as Alicia Keys, Cee Lo Green, Dave Matthews and the Foo Fighters. For his gig with Obama, Jon Bon Jovi even caught a ride on Air Force One.
"Let's face it: They help raise the money that you need to wage a serious campaign," said Robert Schmuhl, a professor of American Studies at the University of Notre Dame who has written about the intersection of politics and celebrity. "Most Americans today are involved in what we call the 'celebrity culture' anyway. They understand how it works."
One way Obama makes it work: Raffling access to donors, and not just to dinners with him, but ones that also offer star power at private affairs like the one at Parker's house. The contests typically ask donors to give $3 or whatever they can spare.
The Obama campaign calls it a way to lure in donors who may not otherwise be involved in politics at all. Throw in Clooney, and watch the dollars flow.
A fundraising dinner held at the star's house last month drew an eye-popping $15 million, with more of it coming from a low-dollar raffle than tickets to the event.
That result showed how Obama's team, using Web ads and social media, is using celebrity to raise money from people who will never get in the room.
Implicit in the arrangement is that access to Obama, the president of the United States, is not enough of a draw. Obama's campaign has gone so far to make its next "Dinner With Barack" raffle more enticing by telling would-be donors that they can help pick Obama's guest — naming Clooney and Parker as examples.
All the star wattage comes as Obama's campaign is warning supporters that they need to give. Central to Obama's strategy is having a larger number of people giving small-to-medium donations.
"The other side has the money," campaign manager Jim Messina said in one appeal to donors. "They know they can buy the election if they spend it."
But Hollywood has the money, too.
"There's a reason it feels like he's been here every two weeks for the last two years," Carrick, in Los Angeles, said of Obama. "Every time we turn around, there's someone on the radio telling you that you have to drive around the motorcade traffic."