Yes, really. The White House has a lot of chimneys, and while they might be used less these days than when the structure was originally built, the big building still requires plenty of heating to stay warm during those cold East Coast winters. Jeff Schmittinger was the White House chimney sweep since he started in the Clinton administration. He refused to accept any money for the gig all the way up until his retirement in 2017.
He kept an old-fashioned chimney sweep costume in case someone wanted the full, classic experience. Jeff’s website features a picture of him in full regalia, on the White House roof, holding an American flag.
Assistant to the President and Principal Deputy National Security Advisor — $180,000
It's not unfair to say national security is one of the more important tasks of the president, which is why the National Security Council is so stacked with members. The Principal Deputy National Security Advisor is responsible for being the Executive Secretary to the National Security Council Principals Committee and the chairman of the National Security Council Deputies Committee.
The role does tend to change depending on what is needed in the council. There are often numerous deputies – there's a lot of work to do. For all that work, this role commands the price of $180,000 per year.
White House Counsel — $180,000
Officially known as the Office of Counsel to the President and Vice President, this role was created in 1943 and is responsible for advising on all legal aspects of policy questions, legal issues, ethical questions, financial disclosures, and quite a bit more. With all that big responsibility, comes an even bigger check of $180,000 per year.
Although this role is to offer legal advice to the president and vice president, the counsel is in an official capacity without serving as an attorney for the White House. However, some amount of controversy has arisen due to attorney-client privileges.
Portrait Artist — $500,000
The White House portrait artist might not take down an annual salary, but they still get plenty of work, since they will often paint presidents, first ladies, vice-presidents, and second ladies. They are commissioned per portrait, and it's a weird gig.
President Theodore Roosevelt destroyed the first painting Theobald Chartrand presented, stating it wasn't masculine enough. For the Teddy Bear, that's a pretty easy mistake to make. President John F. Kennedy's portrait was done posthumously, so painter Aaron Shikler had to piece it together from photographs of Kennedy's face, and used his brother Ted as the body.
Executive Pastry Chef — $100,000
No, there isn't anything that much strange about a pastry chef, but if you're a chef in the White House, you need to be the best. You might be tasked with making birthday cakes for kings, queens, presidents, or popes. You might have to build a five hundred pound gingerbread house, and you have to be ready to jump into action at all times, in case the prez needs something to nosh on or there's an emergency meeting that needs catering.
The Executive Pastry Chef also maintains the White House beehive. Like, the kind that has bees inside them. In case there is a honey cake on demand.