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Some Obama Impersonators Still Have Hope

"I'm finding at live appearances that people are holding onto me tighter for photographs. They're warmer, they're grabbing me more longingly."

Reggie Brown doesn't need to figure anything out right away. For eight years, he's been the most in-demand Barack Obama impersonator on the open market. So successful, in fact, that he demands five figures to don the fake ears, plastic mole, and increasingly speckled grey hair at your corporate Christmas party or donor dinner gala. When he's not on the private circuit, you can catch him working sporadic TV appearances on Real Time with Bill Maher and an extended stint as a punching bag on FOX's tremendously lame Huckabee. The Obama act has paid for his house, his retirement, and his life. If the end of Obama's presidency marks the end of his career, he's still in a pretty good place.

"I will have some time to decompress, because it has been a really long run," says Brown, who tells me 90 to 95 percent of the audiences he performs for are conservative. Over the years he's spiked his act with occasional self-deprecation for laughs, but he's always kept his impression respectful. He's even turned down jobs that didn't feel right, like the commercial gig that would've paid him $20,000 to recite fabricated statistics in character. He says he can sleep well at night knowing he's never sold out his belief system for a job.

Over the last eight years, Brown and those of his ilk have never wanted for material. We've seen the promise of Hope that ushered the 44th president into office on a cloud of Change in '08 sour quickly into never-before-seen levels of petty partisan in-fighting and the rise of the Tea Party. There have been Birthers and Beer Summits, Obamacare, and the death of Bin Laden. Now, with his approval ratings edging upward (towering over his predecessor's paltry end-of-second-term 22 percent), and the looming presidency of a man who is seemingly the exact opposite of everything Obama stands for, the men who impersonate him have noticed a shift in tone.

"I'm finding at live appearances that people are holding onto me tighter for photographs," says Dion Flynn, an Obama impersonator who got his start on Late Night with Jimmy Fallon. "They're warmer, they're grabbing me more longingly. I've definitely noticed that. That Trump is our replacement has really brought out some abandonment issues, There's this idea now of 'Wow, we had it really good with this guy and we didn't even know it.'"

For that reason, some Obama impersonators are holding out hope that the entire Donald Trump calamity and the unprecedented election that brought him to power might keep our current president in the headlines far after his time in the White House. Maybe Obama acts will carry a certain therapeutic nostalgia in these uncertain times? Brown, for one, says he's already booked a number of dates throughout 2017. Others aren't so sure Obama's appeal is enough to keep them steadily employed once he's out of the daily limelight, and believe Trump will mean a bust, not a boon, for Obama impersonator business.

"I think Obama in general, as far as commercial entertainment goes, has never been as popular as Bush or Clinton, and part of that is his personality and his intelligence," says Ron Butler, who started impersonating Obama on Jimmy Kimmel Live. "The Trump presidency will eclipse anything that's happened before. So my instinct says that the work is going to die off quickly."

As a backup plan of sorts, some impersonators have begun to use their corporate gigs as an opportunity to network with powerful people. Brown tells me, over the course of his eight years doing his act, he's made friends with CEOs and industry leaders who've offered stepping stones into second careers. Flynn, "not relying on the idea that the Obama will last," has already found a home out of makeup in advertising consulting, a natural extension he says grew right out of his years in show business.

The strangest thing about falling into a career as a person who impersonates the president, these three agree, is you can in no way prepare for it. Someone becomes the most powerful person on earth, and a few people who look like them get their ticket punched to stardom, their lives changed forever. For Brown, Flynn, and Butler, that happened in November of 2008. They're permanently indebted to one man and one movement. For now, no matter what comes next, they appreciate the journey.

"I didn't plan for any of this," says Flynn. "I didn't plan to go to Europe and perform Obama, I didn't plan to do 40 appearances on national television, or do IPOs. I've done crazy unbelievable stuff. All of this is a total gift and a blessing. There's nothing missing."

Brown's latest act reflects how the job of becoming Obama for eight years has changed him, a deeply personal story that morphs his standard 30-minute act into a far more sober hour-long keynote. "It's called 'How I Became The President of the United States,'" the 36-year-old former Chicago reporter tells me. "I still come in with to 'Hail to the Chief' and the Secret Service and everything, but after I hit them with 20 minutes of comedy I start to deconstruct the character. I take off the ears, I start taking off the make-up, and by the end of the story I'm showing them pictures of my life—growing up with a single mother and a Dad who died [when I was] 13—and how I ended up living my dreams through the president as the father figure I never had."

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Correction: An earlier version of this story reported Reggie Brown makes six figures per corporate gig. He makes five figures.