The 15 Wildest, Most Inappropriate Things Donald Trump Has Said On Air With Howard Stern

Voting Rules
Vote up the most insanely inappropriate things the President actually said.

Everyday, there there appears to be yet another blunder, gaffe, or incredibly boneheaded comment coming from the White House. But when it comes to verbal screw-ups and general nastiness, this is not Donald Trump's first rodeo. He has been saying bizarre things for decades – some of them nonsensical, some of them plain offensive, but nearly all of them outrageous. Unsurprisingly, Howard Stern tends to bring out an even more primitive side to Trump; it's almost as if Stern's own pushing-of-the-boundaries gives Trump permission to make the most startling and bewildering statements. And to Stern's credit, it makes for good radio.


It doesn't, however, make for good governance, and the 45th Commander-in-Chief isn't exactly known for his tact or brevity. Oh well, at least there was a time – when we were all collectively a little more naïve – in which these Trump quotes were simply provocative. Love him or hate him, this collection of inappropriate Donald Trump quotes will make even his most loyal of continuants cringe. 

  • 1
    241 VOTES

    He Checks Out Ivanka's Rack

    What He Said: "She's always been quite voluptuous."

    When He Said It: 2004

    241 votes
  • 2
    237 VOTES

    He Thought Paris Hilton Was Hot... When She Was 12

    What He Said: "I've known Paris Hilton from the time she's 12, her parents are friends of mine, and the first time I saw her she walked into the room and I said, 'Who the hell is that?' At 12, I wasn't interested ... but she was beautiful."

    When He Said It: 2003

    237 votes
  • He Praises His Own Uninvolved Parenting Style
    Photo: Wikimedia Commons / CC-BY
    193 VOTES

    He Praises His Own Uninvolved Parenting Style

    What He Said: "I've never--I've been a good father but I--or rather, I've been a good father, a really good father, but I've never been that involved. Like, if they ever said, come on outside, dad. Let's have a catch in Central Park ... I'd say, excuse me, what?"

    When He Said It: 2004

    193 votes
  • He Has A Remarkably Stupid Idea To Fight Terrorism
    Photo: flickr / CC0
    177 VOTES

    He Has A Remarkably Stupid Idea To Fight Terrorism

    What He Said: "You have a red button in the plane and the pilot has a huge problem in the back. He's got two or three terrorists, you know, crazy. ... He presses a button and sleeping gas comes out, the entire back of the plane goes to sleep."

    When He Said It: 2002

    177 votes
  • 5
    216 VOTES

    His View Of Beauty Is All About What Is – Or Isn't – On The Chest

    What He Said: "A person who is very flat-chested is very hard to be a 10."

    When He Said It: 2005

    216 votes
  • He Admits To Not Taking Care Of His Children (Or, Barron Who?)
    Photo: flickr / CC0
    190 VOTES

    He Admits To Not Taking Care Of His Children (Or, Barron Who?)

    What He Said: "I mean, I won't do anything to take care of them. I'll supply funds and [Melania will] take care of the kids."

    When He Said It: 2005

    190 votes