JON STEWART – NEW YORK, $20 MILLION

Before he made his way into the entertainment industry, Jon Stewart worked a variety of jobs, including busboy, shelf stocker, and even bartender, to cover his personal loans. Well, all that hard work eventually paid off when he found success as a comedian. He then found even more success as The Daily Show’s host, a gig he kept from 1999 to 2015.

Thanks to his successful career, Jon has had the chance to call this lovely New York penthouse his home. Bought in 2005 for $5.8 million, the property provides 6,280 square feet of living space, five bedrooms, a media room, a library, and has access to an observation terrace, providing its residents with a breathtaking view and overall relaxing atmosphere. In 2014, though, Jon placed the pad up for sale for $17.5 million, but that price rose to $20 million in 2017.