Top 10 Embarrassingly Cringeworthy Moments In Film

Top 10 Films takes a look at some of film’s greatest embarrassingly cringeworthy moments from Travis Bickle’s ill-advised date to the X-Rated cinema in Taxi Driver to American Pie’s moment of…ahem…over-excitement…

Top 10 Embarassingly Cringeworthy Moments In Film

I wonder what embarrassingly cringeworthy moment these boys are watching in American Pie?

To feel embarrassed for a character, or to feel bad for them or at least to feel their shame and their pain is a credit to many different facets of filmmaking. You need excellent writing for the actors, you need the actors to be able to sell it to us and you need the director to put it all together. When done right, you get scenes that make you squirm. We’ve all experienced some of these before and others, thankfully, we haven’t (I don’t think any of us have ever been on LV-426 and have tried to get a foreign entity through quarantine). Here are the top 10 most embarrassingly cringeworthy moments in film.

10. Taxi Driver (Scorsese, 1976)

Travis takes Betsy to a porn theater for a date

Top 10 Embarrassingly Cringeworthy Moments In FilmTravis Bickle, as played by Robert De Niro, is a loner. When he finally gets a date with the beautiful Betsy (Cybill Shepherd), he really has no experience with women, or with people for that matter. He ends up taking her to a porn house and she reluctantly goes in with him after he tells her that he sees a lot of couples at these films. She naturally leaves quickly and he follows her out, shocked that she doesn’t like these films. Right from the moment he goes to pay for the tickets and you see the XXX on the sign, you want to sink away in your chair. It’s painful to watch because you know the date is over even before it begins.

9. The 40 Year Old Virgin (Apatow, 2005)


Top 10 Embarrassingly Cringeworthy Moments In FilmAndy, as played by Steve Carell, is the virgin of the title. One night he is sitting around with his work cronies and the discussion turns to their sexual escapades. His buddies share stories of their experiences and then when it’s time for Andy to tell them about his, he starts into a painful recount of some sex freak that he apparently dated. It starts out a little awkward as he uses lines like ME SO HORNY and says screw instead of the R rated word. And then it gets to the point where you feel terrible for him as he describes the feel of a woman’s breasts as sandbags. You feel bad for him because he’s trying to fit in but he just can’t hide the fact that he has no idea what he’s actually talking about.

8. Can’t Buy Me Love (Rash, 1987)

Cindy tells the truth about her and Ronald

top10films_cringeworthy-awkward-embarrassed-moments-movies_cantbuymeloveCan’t Buy Me Love is a fairly standard story about the jocks and the nerds. But it has a twist. Ronald, played by Patrick Dempsey, pays Cindy, the head cheerleader, played by the late Amanda Peterson, $1000.00, to pretend to date him. This, as he correctly predicts, will elevate him from nerd to icon. At a party one night, she gets really drunk and her college boyfriend comes back and he admonishes her for doing what she did. In a drunken rage she spills the beans about her arrangement with Ronald. You feel for the guy as he is in a room full of people who now not only hate him but are embarrassed that they were fooled. He feels like crawling into a hole and you feel like crawling in there with him.

7. Aliens (Cameron, 1986)

We waste Burke….no offense

Aliens - BurkeThis one is a bit different. This is list is made up of people that you like and root for, Burke from Aliens is the exception. But you can’t help just feeling tense and awkward when you watch the scene where he feebly tries to defend himself by telling Ripley and the marines that they are all paranoid when Ripley accuses him of isolating her and Newt so that he could get them impregnated. He would also have to essentially kill the rest of the marines in their sleep. All of this so he could make a pile of money. The selling point of this scene is the amazing work done by Sigourney Weaver, Bill Paxton (“you’re dead…you’re dog meat pal”) and of course the incredible Paul Reiser, who looks terrified beyond belief but has to at least try to tell his side of the story.

6. Sixteen Candles (Hughes, 1984)

Sam’s grandmother feels her breasts

Sixteen Candles, Molly Ringwald, John Hughes,In the film, Sam’s sister is getting married the same weekend that she has her 16th birthday. As is typical in a John Hughes film, the adults are clueless and they do everything to embarrass the hell out of Sam. When she runs into her grandma and grandpa, they fawn over her and her grandma comments that she has finally gotten her breasts. This makes Sam uncomfortable to begin with, but then her grandmother remarks how perky they are and how small they are, and then she proceeds to feel her up. Sam leaves, mortified and comments to herself, “I can’t believe my grandmother actually felt me up.”

5. Fast Times at Ridgemont High (Heckerling, 1982)

Linda walks in on Brad masturbating

Phoebe Cates, Fast Times At Ridgemont HighThis is one of the most famous and imitated scenes in film history. When Brad, as played by Judge Reinhold, has visions of Linda (Phoebe Cates) getting out of the pool, exposing her breasts and making out with him, he begins to masturbate in the bathroom. But then Linda gets out of the pool, and with her ear clogged, heads to the bathroom to get a Q-tip. She walks in on Brad and catches him in the act. She is mortified and retreats immediately. Brad is shocked and embarrassed and as he sits wondering what just happened, he remarks, “doesn’t anyone freakin knock anymore?” It’s a painful scene to sit through for most guys.

4. There’s Something About Mary (Farrelly Bros., 1998)

The zipper scene

there's-something-about-mary-zipper_ben-stiller_top10filmsTed (Ben Stiller) is a good guy. He’s taking Mary (Cameron Diaz) out to the prom. He’s staring out the window at some birds, while he is using the restroom at Mary’s house. Unfortunately for him, Mary is getting changed in the window right where the birds are sitting. As he realizes this, in a panic he pulls his zipper up to fast and in the process, he gets his man parts stuck in the zipper. I’m already cringing while writing this description. A woman might not fully understand the pain involved in this, but it gets worse. Mary’s mom and dad both come into the bathroom and freak out over what they see. But that’s also not the worst of it. Soon a police officer and a fireman shows up. At this point, in between fits of laughter, you are ready to hide your head in shame. t’s a painfully awkward moment in the film and something that every guy is terrified of.

3. The Last American Virgin (Davidson, 1982)

The bad boy wins…every time

Top 10 Embarrassingly Cringeworthy Moments In FilmGary, as played Lawrence Monoson, has loved Karen (Diane Franklin), literally since he first laid eyes on her. He makes an attempt to ask her out but she doesn’t accept. One of Gary’s friends, David (Joe Rubbo) is hosting a party and it is here that Gary sees his other best friend, the guy with the California playboy good looks, Rick (Steve Antin) hitting it off with Karen. They begin dating and Rick ends up impregnating her and conveniently breaks up with her once he finds out about the pregnancy. Gary, the typical nice guy in the film, offers to take care of her. He pays for her abortion, they stay clandestinely at Gary’s deceased grandmother’s house while she recovers, and he does all of this because he loves her. When all of their friends are returning from a winter ski trip, Karen informs Gary that she is going to have a party for her birthday. It’s at this point of the film that Gary finally confesses his love for her. She finally returns the feelings and they are now dating. Then Gary buys her a necklace, walks into the party, and sees her in the kitchen…..making out with Rick, the guy who dumped her upon her pregnancy. This is equivalent to getting your nuts stuck in your zipper. It’s all in the pit of your stomach. Gary is the nice guy and nice guys finish last. It’s enough to make you depressed and to feel so embarrassed for him. It’s a terribly sad ending but a realistic one.

2. American Pie (Weitz & Weitz, 1999)

Jim blows it…..twice

Top 10 Embarrassingly Cringeworthy Moments In FilmThis is the thing of nightmares for all men, but especially younger ones. The situation is that Jim (Jason Biggs) has his gorgeous foreign exchange student in his bedroom and she is ready to have sex with him. Nadia (Shannon Elizabeth) is half naked and when she has him just barely touch her leg, he ejaculates. This is embarrassing enough and at this point, we all feel bad for him. Jim has never been with a woman and the excitement is too much for him to bear. But it gets better and worse all at the same time. Nadia strips down and he goes in for a second time and again he can’t hold back. At this point you’re not only cringing for him, you’re dying of laughter.

1. Swingers (Liman, 1996)

The start and the end of a relationship via answering machine

Top 10 Embarrassingly Cringeworthy Moments In FilmThis one scene made me cringe more than any other. Maybe it’s because I’ve experienced this myself. The scene has Mikey, as played brilliantly by a pre-Iron Man Jon Favreau, placing a call to a woman he just picked up in a bar. The set up to this scene is that his friends tell him that once he gets a number, he has to wait between two and seven days to call her. This confuses Mike and being that he is desperately trying to get over a six-year relationship, he throws caution to the wind and he calls her the same night. As he tries to leave his number on the machine, it cuts him off and so he calls back to leave another message. It again cuts him off and he calls back. Now he starts going into his painful past relationship and how he doesn’t think he can see this new girl anymore and so on. It’s a scene that starts out being played for laughs but soon enough we are right there with Mike and we can feel his pain and his angst. He’s a very damaged character and he hasn’t had time to heel or process any of the break up and try as he might to get back into the dating scene, it all comes back to his pain and his unstable emotional state. It’s like watching a car wreck in slow motion. You want to do something to help him but you can’t. I felt bad for Mikey. I wanted to do something in that one moment to assuage his guilt and his sorrow and his anguish. But you just watch as he gets the noose tighter and tighter until the girl picks up and tells him to never call her again…

Written & Compiled by Dan Grant

Tell us what your most embarrassingly cringeworthy moments in film are….

About the Author
Dan Grant is an author and horror film fan from Canada. His first novel Terrified and Defenseless is now available for e-download from Amazon. Follow Dan on Twitter @baumer72.

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  1. Avatar
    Dan Reply

    Fun read Dan. Travis’ naivety in Taxi Driver is the pinnacle of awkwardness.

    The end of The Last American Virgin definitely hits home – like a slap in the face.

    Love your choice for number one. It’s a brilliant opening to Swingers.

  2. Avatar
    Callum Reply

    Such a fun list. I haven’t seen many of these but I totally agree with Swingers. That scene is so cringeworthy. You can’t help but feel like shouting at the screen to stop calling. Put the phone down. Let it go! 🙂

  3. Avatar
    Dan Grant Reply

    Thanks Dan for putting it together. I’m glad you agree with the Swingers at number one. That scene just makes you want to crawl into a hole.

    Callum, same thing, it seems like we can all kind of relate to Mikey’s plight.

  4. Avatar
    Nostra Reply

    I was also expecting the scene in Bridesmaids where they had food poisoning.

  5. Avatar
    Roger That Reply

    Great idea for a top 10. There are so many good ones. Porkies has one that springs to mind regarding young men and working girls. Wasn’t there something similar in Last American Virgin too? Of course, Beverly Hills Cop III was embarrassingly cringeworthy but I don’t think that’s what you were getting at.

  6. Avatar
    Dan Reply

    Nostra… the one from Bridesmaids that Springs to mind is the part where the two friends are embarrassingly vying for the attention of the Bride when they are giving they’re ridiculous speeches. I know the part that you mean is all so embarrassing but the one that I’m thinking of actually is a little bit more cringe-worthy in my opinion. I don’t really know what part you mean in Porky’s that would fit this list. There’s a part at the beginning with cherry forever where the boys play a trick on each other or a prank which causes Peewee to run naked. But that wasn’t really cringe-worthy that was just more funny. And there really wasn’t an embarrassing scene in the last American Virgin with a hooker. It would be interesting to see your list as it seems like our definition of embarrassing moments kinds of differs.

  7. Avatar
    Dan Reply

    Sorry the last part of that comment was for ROGER THAT.

  8. Avatar
    Roger That Reply

    I’m trying to remember what happens. There’s a woman who one of the guys delivers pizza to. One day, he and his friends go there. Two have sex with the woman but just as the third is about to get his turn the boyfriend turns up.p and chess them away.

  9. Avatar
    Dimitri Reply

    Embarrassing rather than completely cringeworthy but the scene in the Goonies when Andy kisses mikey thinking it’s brand.

    One that I’d say would make the top 3 is the bit in Class when Rob Lowe walks in on Andrew McCarthy sleeping with his mom.

  10. Avatar
    Dan Grant Reply

    @Roger That….yes, Carmela lol. David and Rick have relations with her and then when it’s Gary turn, Paco, her darling sailor boy comes back….David walks out of the room and remarks, “what a nympho”.. Yes, embarrassing for sure…..good call.

  11. Avatar
    Alex Withrow Reply

    Oh man, what a perfect choice for number 1. That scene kills me every time. Great list over all as well!

  12. Avatar
    Callum Reply

    Been thinking about this top 10 a lot since I first saw it. Has to be one of my favourites from you guys.

    A friend asked me if the scene in Top Gun with Tom Cruise singing to Kelly McGillis in the bar would count. I said it could be embarrassing if it were you doing it, NOT TOM CRUISE!

  13. Avatar
    Dan Reply

    Callum: that’s a really interesting thought. I would love to see somebody else to go this exact same topic. Because I think we all have different opinions about what could be embarrassing or cringe-worthy. So it would be really interesting to see somebody else post their thoughts.

  14. Avatar
    ArchE Reply

    Wonderful selection of pitfalls, faux pas and moments the characters would rather forget.

    Perhaps not one worthy of this list because of its roots in comedy but the reoccurring motif of Biff and manure in the Back To The Future films is all about embarrassing the bad boy. Its first occurrence is spectacular in its execution.

    More in line with the teen comedies above I’m suddenly drawn to a certain Weird Science and a scene involving drinks poured on our nerdy heroes while trying to be ultra cool for the ladies. At least they get their own back come the end by getting the girls!

  15. Avatar
    Dan Reply

    One from my favourite Spielberg movie – Close Encounters of the Third Kind – when Roy is found by his wife in the bathroom sobbing. He’s fully clothed but soaking wet with the shower running. You’re heartbroken for him and the family because he doesn’t know how to cope with what he’s going through but there’s that underlining embarrassment that he himself is failing as a father and a husband – and he’s now reduced to a quivering wreck in full view of his wife and children. It’s quite tragic but cringeworthy at the same time.

  16. Avatar
    Dan Grant Reply

    ArchE: YES!!! The Weird Science scene is a great mention! I kind of forgot about that scene but it is a great one that could have made this list for sure.

    Dan: Now I need to watch Close Encounters again. I too loved that scene…in fact, that movie might be Dreyfuss at his best.

  17. Avatar
    Mark Fraser Reply

    Funny list. Also …

    Rock Hudson getting hammered in Seconds

    Ewan McGregor putting his hand down the worst toilet in Scotland in Trainspotting

    Ewen Bremner waking up in his girlfriend’s parents’ house after having just defecated himself in his sleep, and the following family breakfast scene, in Trainspotting (again)

  18. Avatar
    Dan Grant Reply

    I need to see Trainspotting again.

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