The "Tropic Thunder" star wrote and directed the comedy, in which he plays self-obsessed male supermodel Derek Zoolander, and when he saw an opportunity to ask property tycoon Trump to be part of it, he didn't hesitate.
"We were shooting at the now defunct VH1 Fashion Awards... and as people were coming up the red carpet, we pulled them aside and asked them to talk about Derek Zoolander, and so Trump and (wife) Melania did that," Ben tells The Daily Beast podcast "The New Abnormal".
But as the divisive leader's popularity drops following his handling of the coronavirus pandemic and the Black Lives Matter protests, some film fans think Stiller should cut him out of the project.
"I've had people reach out to me and say, 'You should edit Donald Trump out of Zoolander', but at the end of the day, that was a time when that exists and that happened. There were so many movies (back then) that had a silly cameo from Donald Trump. He represented a certain thing," he shares.
Before he entered the political arena, Trump also famously appeared in films including 1992's "Home Alone 2: Lost in New York" and 2002's "Two Weeks Notice", starring Hugh Grant and Sandra Bullock, and on TV shows like "The Fresh Prince of Bel-Air", "Spin City", "Suddenly Susan", and "Sex and the City".
But Stiller is convinced the former businessman will always be especially thrilled to have been part of "Zoolander".
"There was a funny story that (U.S. TV host) Chris Matthews told me," he adds. "He was interviewing Trump during the (2016 Presidential) campaign and there was a commercial break. 'Zoolander 2' had come out and... was a big bomb, didn't do well... And they'd been talking about nuclear arms or something and what his (Trump's) stance would be with the Russians, and then... Trump brought up 'Zoolander 2' and started talking about why he thought the movie didn't do well."
"And he started going into detail (saying), 'It's just that in the culture people don't care about male models any more'. And Chris found it so interesting that he was so fascinated about why 'Zoolander 2' didn't do well as opposed to what to do with the Russians and nuclear arms proliferation."