--- title: Jon Stewart and David Letterman Return To Tease Donald Trump description: Jon Stewart and David Letterman both came out of retirement to appear at the USO's 75th birthday party at Joint Base Andrews in Maryland. canonical: https://time.com/4320691/jon-stewart-david-letterman-uso-obama/ author: Tessa Berenson article:opinion: false article:content_tier: free article:published_time: 2016-05-06T11:22:31.000Z article:modified_time: 2026-02-22T17:20:19.805Z article:section: U.S. og:title: Jon Stewart and David Letterman Return at USO Bash og:description: And guess who made a Donald Trump joke og:url: https://time.com/4320691/jon-stewart-david-letterman-uso-obama/ og:site_name: TIME og:image: https://static.time.com/v3/assets/bltea6093859af6183b/bltcd46b635ab126ce6/69889219ab6d773add6a9934/uso-jon-stewart-david-letterman-barack-obama-michelle-obama.jpg?branch=production&width=3840&quality=75&auto=webp&crop=16:9 og:image:width: 1200 og:image:height: 675 og:image:alt: 5th anniversary of Joining Forces and the 75th anniversary of the USO og:type: article twitter:card: summary_large_image twitter:title: Jon Stewart and David Letterman Return at USO Bash twitter:description: And guess who made a Donald Trump joke twitter:image: https://static.time.com/v3/assets/bltea6093859af6183b/bltcd46b635ab126ce6/69889219ab6d773add6a9934/uso-jon-stewart-david-letterman-barack-obama-michelle-obama.jpg?branch=production&width=3840&quality=75&auto=webp&crop=16:9 ---  # Jon Stewart and David Letterman Make Return at USO Bash  by [Tessa Berenson](/author/tessa-berenson/)  ## Tessa Berenson May 6, 2016 11:22 AM CUT  Comedian Jon Stewart shakes hands with comedian David Letterman as President Barack Obama and First Lady Michelle Obama watch at the 75th anniversary of the USO at Joint Base Andrews in Maryland on May 5, 2016. Comedian Jon Stewart shakes hands with comedian David Letterman as President Barack Obama and First Lady Michelle Obama watch at the 75th anniversary of the USO at Joint Base Andrews in Maryland on May 5, 2016.Olivier Douliery—Press Pool/EPA  by [Tessa Berenson](/author/tessa-berenson/)  ## Tessa Berenson May 6, 2016 11:22 AM CUT Jon Stewart and David Letterman both came out of retirement to appear at the USO’s 75th birthday party at Joint Base Andrews in Maryland on Thursday, and Stewart couldn’t help himself from making a Donald Trump joke. Introducing Joe Biden, who was there with his wife Jill, Stewart said, “He’s always a guy, you know, we had a lot of fun with … he’s a guy that’s unpredictable.” “He’ll say whatever he kind of thinks of, whatever comes to his mind, sort of impulsive,” the former _Daily Show_ host continued. “Sometimes, you might think to yourself, ‘That sounds crazy,’ or ‘Man, that _is_ crazy.’ And who would have thought that now, that gets you the Republican nomination.” “Don’t worry,” Stewart finished. “Trump’s gonna keep you busy. You’re going to have to repaint all the planes with TRUMP in big gold letters.” Former _Late Show_ host Letterman also spoke at the event, joking, “I’m pretty much ready to go and happy to be out of the house.” ```json [{"@context":"https://schema.org","@type":"NewsArticle","@id":"https://time.com/4320691/jon-stewart-david-letterman-uso-obama/","mainEntityOfPage":{"@type":"WebPage","@id":"https://time.com/4320691/jon-stewart-david-letterman-uso-obama/"},"headline":"Jon Stewart and David Letterman Make Return at USO Bash","datePublished":"2016-05-06T11:22:31.000Z","dateModified":"2026-02-22T17:20:19.805Z","description":"And jokes about Donald Trump were on the menu","url":"https://time.com/4320691/jon-stewart-david-letterman-uso-obama/","keywords":["celebrities","Military","Comedy","Donald Trump"],"thumbnailUrl":"https://static.time.com/v3/assets/bltea6093859af6183b/bltcd46b635ab126ce6/69889219ab6d773add6a9934/uso-jon-stewart-david-letterman-barack-obama-michelle-obama.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","author":[{"@type":"Person","name":"Tessa Berenson","jobTitle":null,"url":"https://time.com/author/tessa-berenson/"}],"articleSection":"U.S.","image":[{"@type":"ImageObject","url":"https://static.time.com/v3/assets/bltea6093859af6183b/bltcd46b635ab126ce6/69889219ab6d773add6a9934/uso-jon-stewart-david-letterman-barack-obama-michelle-obama.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","width":1200,"height":675,"headline":"5th anniversary of Joining Forces and the 75th anniversary of the USO","caption":"Comedian Jon Stewart shakes hands with comedian David Letterman as President Barack Obama and First Lady Michelle Obama watch at the 75th anniversary of the USO at Joint Base Andrews in Maryland on May 5, 2016.","creditText":"Olivier Douliery—Press Pool/EPA","representativeOfPage":true}],"publisher":{"@type":"Organization","name":"Time","url":"https://time.com/","logo":{"@type":"ImageObject","url":"https://time.com/images/logo.png","width":528,"height":156},"foundingDate":"March 3, 1923","sameAs":["https://www.facebook.com/time","https://www.instagram.com/time/?hl=en","https://twitter.com/time","https://www.pinterest.com/timemagazine"]}},{"@context":"https://schema.org","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"/section/us/","name":"U.S."}},{"@type":"ListItem","position":2,"item":{"@id":"/tag/celebrities/","name":"celebrities"}},{"@type":"ListItem","position":3,"item":{"@id":"https://time.com/4320691/jon-stewart-david-letterman-uso-obama/","name":"Jon Stewart and David Letterman Make Return at USO Bash"}}]}] ```