Donald Trump in His Youth: Rare Photos From His Childhood

33. On the Red Carpet

Though Donald Trump has seemed to fall out of favor with Hollywood elites in recent years, he was once a prominent sight at red carpet events all across the country. And can you blame him? He has been a staple of New York’s wealthy elite class since his birth. Trump has appeared in numerous films dating back to 1989, almost always as himself. Of course, his flirtations with TV and movie stardom hit its peak in 2003 when NBC brought on “The Donald” to host The Apprentice.

The reality TV show became a huge hit and helped Trump coin his catchphrase, “You’re fired.” The original show spawned the spin-off The Celebrity Apprentice. It seemed that Trump was once again rubbing elbows with Hollywood elite, but some of those connections have lingered, much to Trump’s dislike.