Tony Stark/Iron Man is many things in the Marvel Cinematic Universe but a perfect person he is not. In fact, he's even one of the most unstable and problematic superheroes in history and some of his decisions have had dire consequences. Even so, he's still the de facto biggest brain in the MCU's first three phases.
What this means is that his usual acts of valor, brilliance, and selflessness tend to overshadow some of his misdeeds. While he is quite ashamed at some of these misdeeds (especially that one with Ultron), there are still plenty of them he's yet to feel shameful for. So, let's commemorate some of Tony Stark's most shameless acts because those are a big part of why we also like him.
24/7 BACHELOR PARTIES
Stark is pretty much the Marvel equivalent of Bruce Wayne from DC. He's a successful business mogul and genius who still has time to be a socialite and surround himself with superficial people to feel a little less hollow inside. With that in mind, before he became Iron Man, Stark has no shortage of parties.
Of course, since he's a bachelor in his prime, these parties tend to be filled with single women who throw themselves at Tony like cats during mating season. Coupled with booze and possibly stronger ways to get intoxicated, Tony lives a fast and restless life at the top of the world before falling back down to the cold, hard ground.
WANTING NATASHA ROMANOFF
A big chunk of Tony's adult bachelor life was looked after by his personal assistant, Pepper Potts. Both of them initially had hidden romantic feelings for each other that they didn't act upon until the second Iron Man movie. Even so, Tony still exercised his playboy tendencies as soon as he saw Natasha Romanoff a.k.a. Black Widow.
Natasha was covertly working for Pepper Potts back then as her legal assistant. She managed to cross paths with Stark one day and the billionaire genius was instantly enamored-- so much so, that he nonchalantly asked Pepper Potts that he also "wants one," something Potts adamantly disapproved.
PROPOSED TO PEPPER AS A PUBLICITY STUNT
When Stark and Potts finally managed to formalize their romance, the two of them made it work well enough despite the lethal threats and overwhelming attention they're getting. Heck, Pepper was even nearly killed in Iron Man 3. Still, their love for each other was undeniable and Stark finally took it to the next level by proposing to her... in an impromptu manner.
If you don't recall, this happened in Spider-Man: Homecoming near the ending where Tony Stark gathered a huge international press conference where he'll supposedly announce Spider-Man joining the Avengers. Spidey refused and Stark had to resort to Plan B, which was to propose to Pepper Potts. Any other partner would have felt insulted but thankfully, Pepper has likely tolerated worse from Tony.
PESTERING BRUCE BANNER
Tony Stark is pretty much an extrovert for most of his screen time in the MCU. That's why when he was paired with a reluctantly introverted Bruce Banner, Stark did his best to pester him. This was a notable interaction between the two biggest brains of MCU in the first Avengers movie.
Stark wasn't just doing it for giggles, though. He also appears to want to see Bruce Banner hulking out. Stark knows full well what causes Banner to turn into the Hulk and even still took it too far by electrocuting him. It's safe to assume he didn't have the Hulkbuster at that point and was just extremely curious at Banner's condition.
CREATING SUPERVILLAINS
Apart from creating Ultron, Tony seems to have no shortage of enemies pulled straight out from his own ribcage... figuratively speaking. Almost all the personal villains he faced in the MCU were a result of his bad behavior or irresponsibility in the past. From the Ten Rings who kidnapped him in Afghanistan to even his own father's friend.
The worst of it all was Aldrich Killian who was but a mere hopeful scientist which Stark punitively dismissed back in his younger days. This resulted in a rather catastrophic future for Stark and it nearly killed all his friends or destroyed everything close to him.
INVITED VILLAINS TO HIS HOUSE
Despite Stark's stunning intellect, he's still careless as heck and doesn't think of some of the repercussions of his actions. He's even put Pepper and other people close to him in danger out of these tendencies. One of the most stupid and bold things he did was invite some supervillains in his own home.
He even gave out the exact address knowing full well that he's also putting Pepper in danger by doing so. As expected, his enemies assaulted his home hard and fast and left him with little time to react. Oh, and he was also not prepared at all for the attack even though he himself invited it. It certainly wasn't his brightest moment.
PUTTING PEOPLE IN DANGER
There are Ultron and Sokovia but Tony definitely chastised himself for those massive blunders. Before those, however, he has been putting people in harm's way already. Sometimes from public fights with his villains and other times, he becomes the villain himself, most notably in Iron Man 2 during a party where he wore his armor and got too drunk.
An even sadder part of that scene is it was actually his birthday party that he ruined. Even Pepper stepped in to stop Tony since he was shooting energy beams already in front of innocents while drunk but this only resulted in a tantrum. Eventually, James Rhodes had to step in to contain the situation.
SIDING WITH THE GOVERNMENT
It's one thing to feel guilty or sorry for the damage you've caused in Sokovia but siding with the government is another entirely. Come to think of it, this was the moment when the Avengers started splitting up. Tony siding with the government to control the Avengers was a rather dramatic change that not many of his colleagues liked.
Even worse was the fact that General Thaddeus Ross spearheading this initiative; Tony should have known better than to trust someone like him, especially after his time with Bruce Banner (one would think that Banner could've informed him). In the end, Tony shamelessly imprisoned his fellow teammates-- some of whom were part of the core Avengers group.
KILL MODE FOR SPIDER-MAN
We're aware that Iron Man has no qualms on not sparing his enemies. In fact, he's been killing in the MCU since 2008. After all, his business and legacy were forged on weapons manufacturing so that's understandable. However, he seemed to have extended this no-mercy philosophy to a high school boy who's barely of legal age, Peter Parker.
It's worth noting that the Spider-Man suits Tony designed for Peter had kill-modes in them which lets Spidey go bloodthirsty on any living thing. Letting a minor go around murdering enemies is not exactly good mentorship. Oddly enough, this probably wasn't even necessary, this kill-mode could've easily been replaced with an incapacitate mode.
SELF DESTRUCTING
One of Stark's biggest problems in the comic books is his alcoholism and it has led to many unfavorable events in his life. MCU successfully captures this side by also giving Tony the same tendency and coupling it with palladium poisoning. That and Tony Stark's life had always been messy.
As a result, he hurt the people who cared about him and pushed them away too while making new enemies and all sorts of poor decisions. Luckily, Tony came back full 180-degrees thanks to the Avengers initiative and a bit of Nick Fury wisdom. In the end, it was all worth it as Tony Stark saved the universe.