The Top 8 Most Awkward Movies in Retrospect to Watch Now

Hey, welcome back! This week is going to be tough; I’m going to warn you now. We are going to look at movies from the past that now, in retrospect, are really awkward or raise some questions like: Why?  These are movies from another time in this world, and in some cases, a time that we can’t believe ever existed.

Look, I put movies on this list that I still love today, but I owed it to both you and myself to be really “honest and unmerciful” as Lester Bangs said in Almost Famous. I’ve included movies that make us uncomfortable or give us douche chills when watched now. The reasons they made the list range from the theme of the movie, the acting in the movie, or in some cases the actor involved went on to commit a double homicide (spoiler alert). Regardless of the specific reason why, I think you will have a hard time arguing with me that every movie I put on here deserves to be on this list. Without further ado, I give you The Top 8 Most Awkward Movies in Retrospect to Watch Now.

8. Footloose:

Basically, Footloose is on this list for the scene above. The fact that this was supposed to be taken as some serious, poignant scene is too much to take. As a man, I don’t care how many great moves I might have (and I do), the last thing any of us is going to do is dance when life is falling apart around us like it was for young Kevin Bacon in Footloose.

The whole movie in fact, when watched now, is one giant Jackson Pollack of awkwardness. The main girl whom we’re supposed to root for is a little too promiscuous. Kevin Bacon and Chris Penn who are supposed to be a couple of bad-asses are gymnasts. Have you ever known a bad-ass male gymnast? The movie is a who’s who of cheesy songs…“I Need a Hero,” “Almost Paradise.” It has ridiculous speeches like this:

“What did David do…..pause…leaping and (with authority) dancing before the Lord?”…yuck.

7. The Naked Gun:

That’s a pretty funny scene you have to admit. Hey look, it’s O.J. Simpson in a dark wool cap and dark clothes, kind of like that one night where he allegedly….OK, you get the idea why we’re here. Is there any way to watch this movie today and not feel that at any moment Judge Lance Ito and Marcia’s Clark’s awful perm are going to show up? Pre-murder, this was definitely a movie you could watch today and still laugh. Now if you watched it with your child or someone and they laugh at O.J. and ask you who that is, it would turn into a horribly awkward moment where you would have to hit pause, and talk about what O.J. did, followed up with questions about why someone would hurt  another person and how the world isn’t all ice cream and rainbows. Not cool, O.J. Thanks. This movie is never on TV now, so how about for a moment here, we all look at my favorite part of the movie:

I was only going to show that clip, but then I laughed watching it, so I wanted more:

And for good measure:

Thanks a lot, O.J., because you robbed all of us from ever seeing this movie shown regularly on TV again.

6. The Godfather: Part III:

I can’t believe I’m even acknowledging that this movie ever happened– because really it shouldn’t have ever happened. I mean, The Godfather and The Godfather: Part II are as close to two perfect movies as one can get. They’re fantastic, and even almost 45 years later still hold up so well. We can all blame Winona Ryder for this:

She was originally supposed to play this part, but backed out at the last minute claiming to be sick. So to recap, Winona Ryder’s responsible for ruining The Godfather Trilogy and almost derailing poor Johnny Depp’s career. As we all know, karma caught up to her in the late 90’s with her bizarre shoplifting scandal. Anyways, I put Part III on this list just so I can take another opportunity to bitch about how utterly awful Sophia Coppola is in the movie. I don’t want to sound like a prick, but even if she  finds a cure for cancer one day, it still won’t make up for this movie (fast forward to twenty years from now when we’re standing with our hands held high with the announcement that Sophia Coppola has cured my cancer).

I mean, first off, she’s in love with her own blood, her first cousin, not some second cousin twice removed or something, but literally her first cousin…ewwwww…gross. Second, Andy Garcia is a somewhat respectable actor, and the fact that he had to act in scenes with someone who is that bad at acting must have been torture. I imagine him walking off the set quietly, going into his trailer, looking at himself in the mirror and thinking: “ I can’t do this… I can’t do this…No, Andy…you can…Just do your best…..F**king Winona Ryder. I will get back at her if it’s the last thing I do on this planet.”

It’s not as if he could go to the director with his concerns in this situation since the director was also her father. So we have first cousin gross love and we have the worst acted part in the history of cinema, yet somehow when it came out it was praised as a good movie and nominated for the Best Picture Oscar. Talk about an industry getting on their collective knees for Francis Ford Coppola…I mean, my god, what were they thinking?

5. Big:

OK, yes, this is one of the greatest movies of all-time, no question. I love this movie, but you do have to admit that there are some creepy elements in this movie, mainly the fact that 40-year-old Elizabeth Perkins is sleeping with a 12-year-old boy. I mean, if this were made with a 12-year-old girl and her character had sex with Alec Baldwin, people would have looked on horrified, right? I just think this movie gets banned if the character were a girl and I know Jennifer Garner made a Big-esque movie, but I don’t think the stakes were as high with that movie as they were with Big.  What was Elizabeth Perkins thinking when Tom Hanks turns back into a boy at the end of the movie?…”Oh, shit…I should probably drive away because:  A. I think I’m a pedophile now and B. This kid has been missing for a long time and a neighbor is probably going to write down my license plate.”

What happens when young Tom Hanks goes back to school now after being Big? Since he’s already gotten laid, does he go around trying to bang all the junior high girls and get a bad rep? Does he go on to be a teenage father and become “that kid”, the 15-year-old with a kid and a crude moustache?

4. The Toy:

Any time you can have a rich white man buying or renting a black man for his bratty son, you’ve got comedy gold, right?…Yeesh… Richard Pryor is great and a legend, but even that doesn’t save this movie from being so uncomfortable to watch in hindsight. I think this begs the question of: Could this be made today without raising any eyebrows? And the answer would have to be no although I could see Donald Sterling trying to reboot this franchise wherein he could play the Jackie Gleason role and Justin Bieber could play the snot-nosed punk kid. I mean, let’s be honest, couldn’t you see Justin Bieber trying to pull a stunt like this?

3. Moonwalker:

This one hurts…I loved Michael Jackson and I loved this movie, but as time moved along through the 90’s and 00’s, this movie became more and more….uncomfortable to watch…Fast-forward to the 39-minute mark and watch for a couple of minutes, so I don’t have to explain in great detail why it’s so awkward…

Michael Jackson should have had every print of this movie destroyed after his first trial, but alas it lives on, and now it’s hard not to feel the creeps when you’re watching Michael Jackson run through a field unsupervised with a group of kids and taking one into a secret lair, even if it is to catch Joe Pesci making drugs to take over the world. Based on what we know about M.J., it’s safe to say that he had complete creative control on this movie. This was the absolute height of his reign as the king of pop, so even though it was creepy, he didn’t have anybody around him who would challenge him creatively or anybody who would tell him that the kids subplot thing was a little red-flaggy…This also, I think, is right at the start of M.J.’s goal to have tons of plastic surgery to look like a Who from Whoville.

At the very least though, the “Smooth Criminal” video is dope…and the claymation rabbit at the start of the movie is pretty sweet, too. Watching “Man in the Mirror” at the start of this movie, it’s really jarring to think how popular Michael Jackson was. I mean, he was so beloved that the majority of the world literally turned a blind eye to him transforming into Wacko Jacko. Even when he jokingly grabbed his child Blanket (LOL), and dangled him over a hotel balcony, people made excuses for him. So yeah, Moonwalker is uncomfortable to watch, but at least Captain EO is safe.

2. Little Darlings:

This whole movie makes you feel uncomfortable watching it. It’s like a young girl’s version of Porky’s, which is not a good thing…and I feel sketchy even typing that. At one point, Armand Assante is playing a camp counselor in his thirties who touches campers playfully, drinks beer with one of them, and kisses one of them goodbye on the lips. I think every single “To Catch a Predator” suspect on Dateline had this movie in his backpack with boxed wine and other creepy toys. I don’t think there is another movie that you could really even compare this to in terms of subject matter.

I mean, in some respects, it’s more real in terms of how the kids talk in the movie and how they smoke. It’s just really jarring to watch now. You know what else is jarring?…Watching a pubescent Matt Dillon trying to score with a pre-teen. (Warning, if you live in the Bible Belt, I think it’s a felony to watch this clip…You’ve been warned.)

What was the mood on the set that day? Was everyone involved creeped out? Did any of the key grips threaten to walk off the set in protest? Were people excited to make this movie when the script came out, with the producer saying something like: “Hey, you have to see this script I just got my hands on. This is the movie of all movies on pre-teen girls trying to lose their virginity; this is going take us right to the top of the Pedophiles of Cinema charts.”?

This movie is a relic from a different time and space, and I can’t imagine anything like this ever being made again.

1. Soul Man:

“He didn’t give up; he got down”…yikes… I’m pretty sure this movie killed the careers of C. Thomas Howell and Rae Dawn Chong.  I mean, wasn’t “black face” socially unacceptable by the 80’s? With that said, my mom let me wear black face as Michael Jackson for Halloween in 1988, so I guess I was a part of the problem as well.  I wonder if James Earl Jones’s agent just agreed to let his client do this movie because he got a fat sum of money. Or maybe the director somehow convinced him that the movie was actually going to be very poignant and would teach America in 1988 how to laugh at racial stereotypes…mission failed….officially.

I don’t think I could watch this movie with one of my African American friends…I wouldn’t be able to make eye contact, and I would probably be apologizing excessively throughout the movie. Do we think C. Thomas Howell did the douche actor thing where he “studied” for this role… like he went to shadow some black dudes around town, studied their movements, their mannerisms, anything he could pick up to help him with this role? Maybe like Daniel Day Lewis he stayed in character even off camera. I’m thinking Robert Downey, Jr. in Tropic Thunder based that character on C. Thomas Howell.

At what point during this process did everyone realize that this was going horribly wrong? I would love to know who the first person to contact his agent to see if he could get out of the movie was.

This movie tops the list here because it’s so outrageously over-the-top racist, incorporating black-face and lazy stereotypes. Even for the time that this came out, it was rightfully pissed on.


So there you have them. I hope you enjoyed reading this. If there is a movie that you feel should be on this list, share it below in the comments section. Thanks again for stopping by.

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