20 Of The Most Uncomfortably Awkward Photos Of Trump Before He Was President
No matter how you feel about the current president, you’ve got to admit that Donald Trump is a bizarre guy. Between late night tweet storms and his obsession with fast food, he’s got some usual habits. Not to mention all the strangeness that has arisen from his time as a reality star and cameos on TV and in movies. Overall, it’s a lot of weirdness associated with Trump.
Even before he became president, Trump was one of the most widely photographed people in the world. For better or for worse, all his past weirdness has resulted in some truly bizarre photos. Thanks to the internet, these pictures have been immortalized forever for future generations to look at and ask, “WTF?”
Here are some of the most baffling pre-president pictures of Trump that the internet has to offer.
1. This pic is more than a little ironic.
Doves have long been a symbol of hope and peace. Considering Trump has picked fights with world leaders, celebrities, politicians, journalists and random citizens, it’s pretty ironic. This picture was taken for the cover of a 1985 issue of “Manhattan, inc.” Still, there’s no real explanation as to why they felt he needed to be holding a bird.
2. Just plain creepy.
Even before he became president, people have expressed concern over Trump’s relationship with daughter, Ivanka. He has made several comments saying he would be dating her if he wasn’t her father. The most creepy, though, are the pics of the two together when she was young. Here she is sitting on his lap, gazing at him while caressing his face. Not the father-daughter picture you’ll usually see.
3. A really unlikely pair.
His long history as a public figure has resulted in Trump making friends with many random celebrities. One such friend was the King of Pop, Michael Jackson. They met in 1988 before Jackson performed a benefit concert at Madison Square Garden. Trump has been a staunch defender of Jackson during his most controversial years, which makes sense when you compare Trump’s own problematic past.
4. This photo oozes bad vibes.
Trump’s time as the host of “Apprentice” and “Celebrity Apprentice” also made for strange bedfellows. Gene Simmons, Dennis Rodman and Snooki are just a few candidates the show saw. Former Sandra Bullock spouse, Jesse James also appeared on the show, which led to this cursed image. It should be mentioned that James was exposed for dressing as Adolf Hitler and collecting Nazi paraphernalia while Trump has been extraordinarly sympathetic towards Neo-Nazis and White Nationalists.
5. A photo almost as chaotic as the Trump White House.
Speaking of “Celebrity Apprentice,” the show was a straight up circus. Considering who the ringleader was, it’s not at all surprising. This promotional picture from 2014’s 14th season of the reality show paints a chaotic scene with Trump un-photogeniclly shouting his catchphrase in the center.
6. Just hanging out with a giant T; nothing weird to see here.
To put it lightly, Trump is obviously vain. He puts his name on everything he can and erroneously claims that it’s the best, most luxurious and most elite in the world. This 1996 photo of Trump leaning against a giant T might be the most normal picture on this list.
7. This picture gave us nightmares.
Trump has been quoted as saying that his love of fast food comes from the clean conditions the franchises must maintain. Obviously he’s never worked for a fast food chain but he has starred in a few of their commercials. Which is where this extremely haunted picture of him and Grimace from Mickey D’s. We’ll never look at this friendly purple guy the same way again.
8. Get a load of the ego on this guy.
Season 14 of “Celebrity Apprentice” seems to have been a banner year for the reality TV show. In another promo pic for the show, Trump plays a conductor of the Apprentice candidates choir. We know how much he likes to be in charge but he’s no better at being a maestro than he is a president.
9. Just a casual photo courtesy of The New Yorker.
Since he started his campaign for president, Trump has become increasingly anti-media. However, this is very different than his previous relationship with news publications. Before his presidential run, he never turned down the opportunity to be featured on TV or in print. In 1997, a feature in “The New Yorker” of the future president came with this photograph. In it, Trump — dressed in a suit and with hands in pockets — causally hops on a golf course. Totally normal stuff.
10. The man sure does love a cameo.
You might not know this, but there’s a reason Trump was in do many movies and TV shows during the 90s. It’s not because he’s a good actor but because he negotiated cameos in any piece of media that filmed in one of his properties. This is how we get this bizarre picture of Trump and the flashy girl from Flushing.
11. Greetings from Scotland.
Golf is one of those sports that is associated with wealth and Trump likes to think of himself as a great golfer. There’s no proof behind his belief but he has played on many around the world. Which brings us to this strange photo of him flanked by two bagpipers in the Scottish countryside. There’s no telling what’s so interesting on the ground, though.
12. Not sure what’s going on here but yikes.
One victim of Trump’s famous Twitter temper tantrums is the television comedy show “Saturday Night Live.” It’s pretty ironic when you remember that Trump hosted the series twice. During his 2015 hosting gig, he played himself in a sketch about the fictional restuarant Donald Trump’s House of Wings. This is a fictional commercial but could easily be real given all his failed business ventures.
13. An improvement on his usual look.
His stint hosting “SNL” in 2015 was a ploy to make him seem relatable and good natured. This included a promo commercial with that week’s musical guest, Sia. In the promo, Trump sports a Sia-like two-toned wig and is joined by Kate McKinnon. Despite this promo, we are now very aware that Trump is definitely not relatable or friendly in the least.
14. Trump family photo.
Trump loves a photo-op, no matter how weird or irrelevant it is. This photo is def both weird and irrelevant. During a 2006 recruiting search for “The Apprentice,” Trump stopped by Universal Studios Hollywood for some strange reason. That appearance led to a picture of him with Eric and Don, Jr. — we mean, Frankenstein’s Monster and a zombie.
15. Don’t show up with these at the next asado.
As we mentioned before, Trump has had several failed business attempts; which is weird for someone regarded as a business mogul. One such failure was his Trump Steaks. Though promoted as “the world’s greatest steaks,” reviews for the cuts of meat were extremely bad. Jerry Levin, the CEO of Sharper Image where the products were first carried said they “literally sold almost no steaks.” Color us not surprised.
16. Not a good look.
Rudy Giuliani and Trump have been friends for a long time. Years before Giuliani became his lawyer, he made New York accessible to future president’s construction needs. That’s how this picture was made possible but it doesn’t explain why we’ve been forced to see it.
17. Disturbing on so many levels.
As we said, the relationship between Trump and his daughter, Ivanka, is pretty… different. We easily could have loaded this list with pictures of them but we could only stomach two. We don’t know if it’s his possessive arm around her, the weird look he’s giving the camera or because she’s practically in his lap while they sit on the bed, but this picture bothers us in a very real way.
18. We’re still waiting on those tax returns.
Since he claims to be so rich, a picture of Trump with armfuls of cash shouldn’t be very weird. Actually, it is pretty weird when you take into account that it’s not his money. You know the old Trump motto: why use your own cash when you can play with someone else’s.
19. There’s something eerie about this photo.
Not sure if it’s the focal length of this photo, the weird backlighting or the dead eyes, but this picture is haunting. Taken for the opening of his Taj Mahal Casino, maybe this picture was an omen. After all, the casino closed in 2016 and only sold for 4 cents on the dollar that Trump spent on it.
20. Finally, this work of…uh…art?
Remember what we said about Trump being vain and egotistical? Yeah, here’s a portrait that proves the point for us. Painted by Ralph Wolfe Cowan, this portrait is titled “The Visionary” and is almost as complimentary of Trump as he is himself. It currently resides in Trump’s residence of Mar-a-Lago because of course, it does.