Donald Trump Made His Late-Night TV Debut 40 Years Ago — and It Wasn’t Planned
What To Know
- Donald Trump’s first late-night TV appearance occurred spontaneously on October 1, 1986, during a segment where David Letterman accompanied tourists around New York City and visited Trump Tower.
- Letterman and the tourists unexpectedly met Trump in his office, leading to a humorous, unscripted exchange that included jokes about Trump’s schedule and his USFL team.
- Trump later became a frequent guest, appearing on Letterman’s shows over 30 times.
President Donald Trump made his late-night TV debut on October 1, 1986 — 40 years ago this month — and it wasn’t even planned.
So, how did the real estate mogul-turned-POTUS end up on Late Night With David Letterman? It all started with the host approaching a couple from Kentucky, Tonya Anderson and Neil Bordy, who were visiting New York City for the weekend.
Anderson and Bordy agreed to allow Letterman and his cameras to follow them around for the day. As the tourists took in the sights of NYC, Letterman tagged along to the Empire State Building, helped them make a postcard, and even stopped by Trump Tower.
When Letterman asked the couple if they were familiar with Trump, Anderson recalled what she learned in a 60 Minutes segment. “He’s shoving people out of their homes,” she told him as they rode on an escalator.
The group also chatted with a security guard at Trump Tower, with Letterman jokingly asking him to show them his gun.
Ultimately, Letterman learned that Trump was at Trump Tower that day and was granted a meeting with him in his office.
“I need to talk to you about the heating in my building,” Letterman joked after shaking hands with Trump and being invited in.
The late-night host also searched under Trump’s desk, quipping, “Don, where is Doug Flutie, for heaven’s sakes?” referencing the quarterback of Trump’s USFL team. “Doug!?”
Before he left, Letterman had one question for Trump: “It’s the middle of a Friday afternoon. You didn’t know we were coming. You said, ‘Come on up,'” he said. “How busy can you be?”
To that, Trump admitted, “You want to know my truth? I have nothing to do. I wish I had more to do.”
Letterman also joked on the way out, “There’s a spot over here, Don, on the carpet. Look into that.”
In December 1987, Trump made his first scheduled appearance on Late Night With David Letterman. He went on to appear on that program and The Late Show with David Letterman more than 30 times.
Conversation
Please read the TV Insider Community Guidelines.
Register or sign in to join the conversation.
Watchlist Easy access to only the shows you care about — all in one simple place
Alerts Only important notifications — when a show is returning, when it becomes available to stream, and more.
Special Offers Exclusive products we release related to your favorite shows and streaming services