Most Cringeworthy Moments From Obama’s Hollywood Gatherings

President Obama has held 40 Hollywood fundraisers since becoming President.

Most recently he was a guest of honor at a breakfast hosted by ‘Spider-man’ actor Tobey Maguire and his wife Jennifer.

With tickets costing $33,400 per couple, the Democratic Senatorial Campaign Committee will have made more from the fundraiser than the $2.4 million gross of Pawn Sacrifice, Maguire’s most recent film .

The night before the Maguire breakfast President Obama was feted at the Bel-Air home of Disney Film Studios Chairman Alan Horn and his activist wife Cindy Horn. In attendance were Disney CEO Robert Iger, Julia Roberts and Barbra Streisand. Cindy Horn asked the President: “When you and the First Lady get into the Presidential limousine, do you think of ‘the beauty in the beast?’

The Disney reference was unintentionally timely in view of the fact that earlier that week the debate over who will be the next CEO of the House of Mouse was ignited by the unexpected departure of Thomas Staggs. Staggs was considered to be the heir apparent to Iger, who is expected to step down in 2018, as Disney COO.

The Disney timing issue is not the only awkward occurrence to have befallen an Obama Hollywood fundraiser. In fact the occasions have been characterized by unintentional comedy. Here’s a guide to the most cringeworthy celebrity gatherings:

Gwyneth Paltrow thinks President Obama is very handsome! Hearing this, the most powerful man in the world blushed!!! pic.twitter.com/xM63Ys9kXE

— Movies Now (@moviesnowtv) October 18, 2014

When: October 2014

Host: Gwyneth Paltrow

Guests: Julia Roberts and Bradley Whitford

Cost:$32,400

Awkwardness: Oscar-winning actress Paltrow felt guilty she wasn’t able to do more for President Obama’s 2012 re-election campaign as she was living in London. So she held a cocktail reception and dinner for him a few years later in the backyard of her Los Angeles home. “I am one of your biggest fans, if not the biggest,” Gwynnie gushed. “You’re so handsome that I can’t speak properly.” Obama changed the subject from his looks to the plight of Ebola, citing his hostesses’ children in a plea for the world to find a cure for the disease: “I want to assure everybody that the likelihood of any epidemic here in the United States is extraordinarily small, but there’s a humanitarian crisis that’s happening right now in West Africa where children not much older, and in some cases younger than, Apple and Moses are dying on the streets alone.”

When: July 2015

Host: Tyler Perry

Guests: January Jones and Jason Collins

Cost: $33,400

Awkwardness: Film director Tyler Perry opened up his Beverly Hills home for President Obama but when it came to his remarks to West Coast celebrity comrades, POTUS must have wished for a second take. Obama said, “We should be reforming our criminal justice system in such a way that we are not incarcerating nonviolent offenders in ways that renders them incapable of getting a job after they leave office,” Obama said. His audience reacted awkwardly to him referring to prisoners “after they leave office”; some laughed, others clapped. The President said he’d made a “Freudian slip.” The embarrassment continued. As he discussed the debt incurred by students, an unidentified small child squealed “owww'”according to The Wrap.

When: September 2015

Hosts: J.J. Abrams, Ed and Robin Berman and Michael Smith

Guests: Jamie Foxx, Reese Witherspoon and Kate Hudson

Costs: $15,00-$33,400

Awkwardness: President Obama was in full fundraising franchise mode, attending three events to boost Democrat coffers. The day kicked off with a roundtable discussion at J.J. Abrams’s LA home. In a location that could have been straight out of his 2011 film “Super 8”, the pooled press were exiled to the attic of “Star Wars: The Force Awakens” director’s home. According to a pooled report from Gardiner Harris of the New York Times, things soon got out of control: “Greg Jaffe of the Washington Post is presently crooning Barry Manilow’s “Mandy”…a Secret Service agent had to ask Greg Jaffe several times—the last time somewhat forcefully—to put down the mic and leave the premises.” Obama quickly fled Abrams’ house to see a performance by Jamie Foxx.

When: September 2013

Host: Harvey Weinstein and Georgina Chapman

Guests:
Jessica Biel and Tommy Hilfiger

Cost:$30,000

Awkwardness: Against the backdrop of mounting scandals on Benghazi and the IRS, President Obama was feted at the New York home of independent film mogul Harvey Weinstein, one of his two East Coast cheerleaders (Vogue Editor Anna Wintour is the other one.) He played to the gallery saying, “My thinking was when we beat them [Republicans] in 2012 that might break the fever and it’s not quite broken yet…they’re fearful of their base and they’re concerned about what Rush Limbaugh might say about them.” According to the official press report, some celebrities proved a distracting presence: “Pooler saw Justin Timberlake wearing trendy glasses with thick black plastic frames and his hair was parted on the side and slicked back.”