There can be a lot of reasons to have your picture taken with a person and there can be a lot of reasons that you wish that picture later didn’t exist. In the case of our the current President of the United States, Donald Trump, we think that they are probably more complex than any other leader in the history of the country.
Most people simply want their picture taken with a celebrity and for many years he was just that. He was a real estate developer with off-the-charts charisma and borderline cartoonish need for attention. He was known as a ruthless negotiator, lover of the ladies and supporter of liberal causes. Trump wasn’t an A list celebrity, but certainly bumped up into B+ territory. He was a harmless buffoon and a picture with him was an interesting conversation piece for your wall.
What follows are people who range from barely knowing Trump to being great friends with the President. They are people who love the man to people who loathe him and they are people who were once friends, but flipped when they say he did. Whatever the case, here are 15 people who were pictured with Donald Trump, but wish you didn’t know.
15 Megan Mullally
It probably sounded like a really funny idea at the time, but now it’s going to be a picture that will come back to haunt her career again and again. It still sounds like a cute idea. Get the guy who has the reputation as the billionaire with the giant ego together with the woman who played the spoiled egotistical princess on TV and put them together to sing the Green Acres theme song. That was a late 1960s show starring Eddie Albert and Eva Gabor about a couple of rich socialites who moved to the country to own and operate a farm. So, Mullally and Trump sang the song at an awards show, it was suitably awkward and everybody moved on, right? Yeah, until he was elected as the most powerful person in the free world and she sang with him. Now this very liberal woman in real life is going to have to explain this situation to people every day until the end of time.
14 Macaulay Culkin
It’s hard enough to be a child star, but to be a child star with parents who do not have your best interests in mind makes things even rougher. Such was the case for Macaulay Culkin. Then, toss on the fact that he was in one of the most popular children’s Christmas movies of all time, only slightly more popular than its sequel. The success of the Home Alone movies was so big, it made casting agents see Culkin only as 8-year-old rascal Kevin McAllister. The rest of his movie career, extending into his adulthood was little more than the occasional independent cameo role when a friend would throw him a bone. Not to mention, well, he didn’t exactly grow into a good looking man. So Culkin puts up with all of this and then all of sudden, in mid-2016, he’s thrust back into the spotlight because of a 20-second cameo in Home Alone 2 where he briefly talks to the future President of the United States. It was part of a script. They were both paid, but suddenly, Culkin’s biggest hits on the Internet are in memes of his 10-year-old over-acting self with Donald Trump. Poor kid...err.. 35-year-old man.
13 Snoop Dogg
Snoop Dogg is one of the couple dozen celebrities who is self aware enough to recognize that they have painted themselves into a corner by creating a quasi-character of who they actually are, but instead of being pissed off about it, have fun with it and roll with the punches. Donald Trump was one of these people until the day he recognized a lot of America wasn’t in on the joke and they might elect him President. People like Snoop and Trump are exactly the ones who Comedy Central have always tracked down for their annual roasts because they have a good sense of humor when it comes to their public personas. They act like the stereotypes they know people want and roasting those stereotypes is hilarious.
12 Muhammad Ali
Ali and Trump were known to run in some of the same circles prior to Ali’s disease forcing him almost completely out of the public spotlight. Ali, like Trump, was against radical Islam and when Trump started talking about the religion on the campaign trail, Ali issued a statement. He said: “Speaking as someone who has never been accused of political correctness, I believe that our political leaders should use their position to bring understanding about the religion of Islam and clarify that these misguided murderers have perverted people's views on what Islam really is." As we all know, Ali died before the election and Trump was one of the first to Tweet condolences. Hopefully his words ring true with not only Trump, but everyone who need to remember that the words “terrorist” and “Islam” are not synonymous. We wonder if Ali would be embarrassed by this photo based on the first days of the Trump presidency.
11 Kareem Abdul-Jabbar, Tony Bennett, Patrick Stewart, Della Reese, Ivana Trump
This is the most awesome photo of people who don’t like Donald Trump that’s ever been assembled to our knowledge. Starting on the far left, you’ve got Tony Bennett, who you kids will recognize as Lady Gaga’s friend. He gave the maximum amount to Hillary Clinton’s campaign possible. Up next is Ivana Trump. There are probably a lot of photos that his ex-wife tore up following the divorce. At least the two of them gave us a super hot daughter. Then you’ve got Patrick Stewart. Last summer, he created a stir when he tweeted the photo of a homeless guy in New Orleans with a sign that said “Give me $1 or I vote for Trump.” Stewart responded “I gave him $5.” Then, you’ve got Abdul-Jabbar, who wrote a brilliant anti-Trump piece in The Washington Post just after the election that all should go back and look at no matter what side you’re on simply to understand where everyone is coming from - understanding other’s opinions is important even if you don’t agree. Last up is Della Reese. She has not gone on record being anti-Trump because she retired in 2014 and doesn’t make public statements but based on her history, we can’t think she believes he’s going to make America great again.
10 Andrea Bocelli
One of the stories to come out of Trump's inauguration festivities was how few musicians were willing to perform because they disagreed with the new president’s political views. That’s cool, although we wonder how many times they’ve performed in stadiums owned by people who don’t share their same political beliefs. Anyway...those who either share Trump’s views or don’t let politics get in the way of a paying gig caught a lot of backlash and most of them were forced to back out or face potential boycotts. You’d love to tell them to hold their ground, like Toby Keith did, but not all have the luxury. Think of the typical Toby Keith fan. Now think of the typical fan of someone like opera singer Andrea Bocelli, who had to back out. Bocelli fans are not Trump fans. If they stop buying tickets, it’s not the Toby Keith crowd that will suddenly start to attend opera. Sometimes, you just have to do what’s best for business. And ironically, it’s only Bocelli who can’t see this photo.
9 Jeb Bush
If this had been a normal election cycle, it probably would have come down to Hillary Clinton vs. Jeb Bush, but Donald Trump made sure early on that the early front runner for the Republican nomination was not going to stay there very long. Trump pounded on Jeb quickly and hard, alienating regular Republicans and sending things into turmoil. This photo of the two candidates smiling and exchanging a friendly handshake is one that we can be sure is not on Jeb’s mantlepiece at his home in Florida. If not for Trump, we could be talking about the Bush family the way we talk about the Kennedys as far as great American political families are concerned. Of course, without Trump, the same could be said for the Clintons. We don’t know if he’ll go on to be a great leader or a horrible one, but we do know he’s already shaken things up in a way history never saw coming.
8 Doug Flutie
If you’re looking to find out what kind of President Donald Trump will be, ask the guys who worked for him when he tried to take on the NFL with the United States Football League. People forget just about many business ventures Trump has started -- and miserably failed at. Let’s hope running the country isn't one of them. “I think he’d be scary as a president,” Flutie, who played for the Trump owned New Jersey General, told a radio talk show prior to the election. “When it comes to political office, you want someone that is able to be a little diplomatic. I think in certain areas he’d do extremely well. In other areas, he’d scare the living daylights out of all of us.” Nate Newton, a different USFL player said on the same show: “That’s who wrecked the USFL. I love a man who can go out and be broke five times and come back and be as rich…or better…the next time. But he ruined us.”
7 Cynthia Nixon
Hollywood is good at putting its foot in its mouth almost as good as it’s putting silicone in its starlets. The place is fake and full of hypocrites and doesn’t seem to understand that while middle America doesn’t mind being entertained by the people on the left coast, it doesn’t need to be lectured about how to live by it. Now, we can debate Trump’s policies all day long, that’s not really what this list, or what this entry is about. Cynthia Nixon is the perfect example of Hollywood’s hypocrisy. She has gone on record saying perfectly nice things about Trump in the past and, as this photo shows, she has even accepted an Emmy from the guy. But, when the singular mind of Hollywood gets together and decides what’s best for the country, Nixon jumped on board. In this case, they all decided to write a letter and ask Trump not to be Hitler, which - aside from the fact he never gave any indication he planned on it - probably won’t do any good. Nixon put her name on there with the likes of Piper Perabo, Jane Fonda, TR Knight, Lizzy Caplan, Mark Ruffalo and a whole bunch of other good actors and actresses who you don’t take political cues from.
6 Arsenio Hall and Clay Aiken
It’s got to suck when your career hits that point where you have to make certain decisions to do projects that will keep you in the spotlight but clearly shows that you are not capable of being the “star” anymore. One of the biggest categories of these projects is reality shows and while probably embarrassing, if you have to do them, landing a network one is probably the best option since you get the biggest audience. Being seen weekly on NBC by tens of millions is better than being seen by hundreds of thousands on the Syfy channel, right Dave Navarro? Anyway, The Celebrity Apprentice has breathed a little life into some B-level celebrities who have shown signs of dropping to C-level and Arsenio Hall and Clay Aiken are two such celebrities. You think they’re going to like answering questions about working with the President of the United States for the rest of their lives? If it’s annoying now, check back with them in 10 years or 20. They’re really going to regret this photo ever existed.
5 Billy Bush
In any other election cycle, a tape released with a candidate saying he liked to grab women by the private parts would force an easy loss. All that tape caused in this election was the loss of Billy Bush’s job. The Today Show anchor, who worked for Access Hollywood at the time the tape was made apparently didn’t act appalled enough for NBC’s tastes, so he was fired. It seems unfair for Bush. He was a journalist, who shouldn’t get involved or make comments in anything the subject of his interview says and if you listen to the tape, all the he does is say things like “yup, yup” like anybody says during a conversation to keep the other person talking. Hopefully Bush got a real nice settlement on his way out the door.
4 Russell Simmons
Rap and media mogul Russell Simmons has been a well-documented friend of Donald Trump for decades, but basically turned all in when he chastised his old pal in a column for GlobalGrind last year prior to the election, saying: “Stop fueling fires of hate. Don’t feed into the rhetoric created by small-minded people. You’re smarter and certainly more loving then you let on... You have been many people’s champ in the past, but now you are becoming a major embarrassment. I know the cheap seats are easy to play to, but you can get them just by being the man I have known for nearly 30 years.” Guess we’ll see if they can mend fences moving forward.
3 Lil Jon
In 2013, Rapper Lil Jon was a contestant on Donald Trump’s reality show The Celebrity Apprentice. In one of their tasks, Lil Jon dressed up like Uncle Sam. Trump, ever the historian, kept mistakenly calling Jon Uncle Tom, considered a racist epithet to most black people. Members of the Apprentice staff kept trying to explain to Trump the problem with what he was saying, but producers reportedly say the future President never quite understood the problem, but when Lil Jon finally spoke up, Trump, to his credit, ceased calling him Uncle Tom. The show has returned with The Terminator hosting. We can only wonder if this means Mr. Hasta La Vista will be eying a run at the White House in 2020. Please God, no.
2 Bill and Hillary Clinton
This is a fun one because it’s from the wedding of Donald and Melania Trump in 2005! During the election there was typical posturing over why the Clintons were invited and why they attended, but according to Hillary, she and Bill went because they were already planning on being in Florida that weekend and thought it would be a good time. They didn’t know the Trumps well, but Donald had been a supporter monetarily and seemed to be on their side in most issues. Trump said he invited the Clintons because he gave to the foundation and knew they had no choice and would have to attend. It seems the wrong reason to invite people to a wedding, but when your life is about posturing, as it is in both the Trumps and Clintons' cases, who knows what really goes on in their heads.
1 Alec Baldwin
We’ve saved our favorite for last. Back in early 2007, Alec Baldwin, fresh off a string of movies that weren’t doing anything for his career and not the best press after a few run-ins with photographers and a leaked tape berating his daughter, was seen taking this photo with Donald Trump. How a decade changes so many things. Baldwin rehabbed his personality over the next decade, most notably playing Trump-like schmuck Jack Donaghy in 30 Rock and becoming the poster boy for being the best possible Saturday Night Live guest host. Those two things converged when he was given the role of Donald Trump on the show. When it seemed like Trump had no shot of winning, he could be as nasty as he wanted. Now, people wonder if Baldwin is willing to commit to four years of Trump bashing. Donald may not have a fan in Alec, but at least there’s always Stephen.
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