The Weirdest Jobs In The White House

A White House usher is a member of the household staff at the Executive Residence, which means they're bound to sometimes accidentally see the president nude. That's what happened to Skip Allen when he caught "The Gipper" naked in his private residence.

He was delivering a top secret document, the story goes, when President Reagan allowed Allen to enter the residence... even though he was totally naked and dripping wet, having just stepped out of the shower. Reagan was allegedly "unfazed" and later teased Allen about the encounter... when he saw the President in his underwear later that night!

White House social aides are typically volunteers from the military that attend social functions (in their finest military attire) and help make guests feel comfortable. They receive no extra pay for this task, but they get to dance and mingle with actors and actresses, literal princesses, and other esteemed guests. The best part about being a social aide has to be the celebrity stories.

Ginger Rogers admitted to one aide that she used to tape her butt cheeks together to make her dresses look better. Jamie Lee Curtis required two aides to fix her broken strapless dress. Chevy Chase told one aide to introduce him as "Clark W. Griswold."

Former White House Chimney Sweep Jeff Schmittinger is a character, for sure. He refused to be paid for the gig, for a start: he volunteered during the Clinton administration, they took him up on the offer, and he kept doing it until his retirement in 2017. He also kept an old-fashioned chimney sweep costume (think Dick Van Dyke in Mary Poppins) in his vehicle at all times, just in case a customer wanted that "experience."

Wearing the costume, he's also the official mascot of the annual German Fest in Milwaukee. The website for his full-time gig ("Wisconsin Chimney Technicians") is super-charming, too, featuring Jeff in his full regalia on the White House roof, holding an American flag.

While not an official position at the White House, the role of Portrait Artist is one that is nonetheless filled with every new elected President. It's a weird, unpredictable gig, too: Théobald Chartran was commissioned to do President Theodore Roosevelt's portrait in 1902, but Roosevelt hated it so much he destroyed it (he thought it wasn't masculine enough).

John Singer Sargent was brought in to do another one, which Roosevelt loved (after giving Sargent a notoriously hard time). President John F. Kennedy's was done posthumously, requiring painter Aaron Shikler to cobble it together from photographs (Kennedy's body is actually his brother Ted's body).

Who says cursive handwriting is dead? It's certainly alive and well at the White House, where the calligraphy office pumps out thousands of ornate envelopes, programs, and place cards every year. Sure, they sometimes use a computer and Adobe InDesign these days, but a lot of what comes out of the office is still done by hand.

Conservatives have made a stink in recent years over how much the official White House calligraphers get paid (about $100,00/year for the Chief Calligrapher), but the documents they write are typically intended for kings, queens, and other illustrious heads of state. What should they do, just use Comic Sans?

Also known as a "Special Assistant and Personal Aide," the President's "Body Man" takes care of their personal needs. The role is sometimes considered to be "part valet, part buddy" and was famously filled by President Obama's so-called "little brother," Reggie Love, from 2008-2011.

Obama jokingly called him "iReggie" in a New York Times interview (“I have an iReggie, who has my books, my newspapers, my music all in one place") and the two frequently played basketball together. Love also kept the President supplied with Nicorette gum while he was quitting smoking.