Supernatural, now on its Season 15, offers fans a lot of footage to look back on. They've followed the loyal Winchester brothers in their quest to save the world, their friends, and each other. While both brothers are heroes, willing to do whatever it takes to help others, they are not without their flaws. Dean, the older brother, can be steadfast and loyal. If he is on your side, he will come to your aid. Still, he tends to be judgmental and harsh like his father John was.

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There are a number of shameless things that he has done over the years. Some are small, and some are large, but they are all--shameless.

Briefly Phased Out His Friendship With Benny

Benny LaFitte in Supernatural

While this friendship did come back, Dean felt that he had to choose between Sam and Benny. Of course, he chose Sam. After having fought for freedom in Purgatory, Benny and Dean developed a brother-like tight friendship. A friendship that left Sam out. So, Sam both judged the friendship and Benny, unable to understand why Dean would be such good friends with a vampire.

Dean decided to end communication with Benny over Sam. Luckily, they started talking again, and Benny ended up sacrificing himself for Sam in the end.

Became a Torturer in Hell

Jensen Ackles as Dean Winchester in Supernatural

When Dean was in hell being tortured, he was offered the chance to be a torturer instead. At first, he turned it down and resisted. However, over time, he took the offer. Unfortunately, this was the first seal needed to break Lucifer out of the cage and start the apocalypse. The seal was to be broken when a "righteous man sheds blood in Hell." Dean, a righteous man, shed blood in Hell when he tortured other souls. Initially, the plan was to turn Dean's father, John, into the torturer, but John never accepted the offer.

Dean hates what he did and feels haunted by it because he is, at the core, noble and good. Still, it was an act that created a disaster.

Insisted (And Insists) His Concerns Are Above Others'

Dean kills Death in Supernatural

Though Dean often has very valid concerns, he doesn't always see others' lives and concerns as just as important as his and Sam's. When Castiel is fighting a battle in heaven, Dean calls him, insisting that Castiel leave the battle to help them.

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In a call with Bobby, he calls Bobby selfish when Bobby doesn't have time to listen to his complaints about Sam. Nevermind the fact that Bobby is trying to figure out how to get his soul back from eternal damnation. Luckily, Bobby calls him out on this, snapping Dean out of his center-of-the-universe mindset, but not all characters are so lucky to have Dean actually listen. Even Death didn't do so well.

Wiped Away Lisa and Ben's Memories

Fearing for their safety, Dean decides to have their memories of him taken away. While Lisa and Ben were definitely not as safe when they were associated with Dean, wiping out their memories without their consent was wrong. We are reminded of another show, Buffy the Vampire Slayer, where Willow, a powerful witch, wiped away her girlfriend's memories (Tara) of their fight. When Tara finds this out, the act is treated like the violation it is, whereas Dean's decision is treated as a great sacrifice and act of protection for Lisa and Ben.

Additionally, although it never happens in the show, it could actually make them more vulnerable to supernatural forces. If something were to happen, they wouldn't be prepared. Likewise, even if they don't know their connection to Dean, demons still do and could have still targeted them to get back at Dean.

Treated Jack Bad, Initially

Jack became a son to Sam, Castiel, and Dean. However, at first, Dean saw him as evil. He wasn't willing to give Jack a chance. No matter how much Jack tried to get Dean to accept him, all Dean initially saw was a threat that he would eventually have to take down.

Later, he warms to Jack, realizing that Jack was just a kid born from unusual circumstances who wanted his three father figures to be proud of him, as well as his dead mother. Dean realizes that they have more in common than he first thought, but his initial treatment of Jack was utterly unnecessary.

Beat Up Charlie

Charlie in Supernatural

When Charlie comes back to the Winchesters and their world from her time in Oz, she comes back as two Charlies. In order to win the war in Oz, Charlie was split into two: Good Charlie and Dark Charlie. However, whatever is done to Dark Charlie happens to Good Charlie. So, as Dean beats up Dark Charlie, the injuries also happen to Good Charlie. When the two sides are made whole, and we have the regular Charlie again, she still has those injuries.

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At this time Dean had the Mark of Cain, which made him more violent, but still it wasn't an excuse to hurt one of our favorite side characters, Charlie.

Left Adam in the Cage

Jensen Ackles and Jake Abel as Dean Winchester and Adam Supernatural

When given the option to bring back either Sam or Adam from the cage where they had been possessed by Lucifer and Michael, Dean chooses Sam. We understand the initial choice. Still, the fact that Adam is never really discussed after, seems strange and definitely shameless.

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Over the seasons, Dean had gained new skills and allies, he could've tried to get Adam out. Fans imagine if it had been John or Mary stuck in that cage rather than Adam, Dean would have found a way to get them out a long time ago.

Tried to Kill Jack

Castiel sits on a bench with Jack in Supernatural

When Jack became nearly soulless and had accidentally killed Mary, Dean saw it as his duty to put Jack down. Chuck/God, gave him a gun that would kill Jack. Dean went after Jack as a thing he hunted, not the son he loved. Dean didn't listen to Castiel at all about Jack, and he barely even listened to Sam.

Luckily, he stopped himself at the last minute. Still, his righteousness and how he treated the other two father figures was pretty shameless.

Shut Castiel Out

Castiel is an all-powerful angel who became not only a great ally and friend, but family. Family is of the utmost importance to Dean, meaning that he would do nearly anything for them. The one thing that he won't do for Castiel is forgive him. Castiel had initially hid Jack's predicament from Dean, fearing how Dean would respond. All that happened Dean blamed on Castiel.

This led to Dean not really caring for Castiel and whether he stayed, or lived, or was a part of their squad. Even Rowena, now the Queen of Hell, saw the switch in behavior as she told both of them to fix their relationship. Hopefully, Dean will heed her words of wisdom.

Killed Amy Pond

Jewel Staite as Amy Pond in Supernatural

In earlier seasons, Dean definitely saw the world in starker hues. You were good or you were bad. If you were supernatural, his job was to hunt you. Amy Pond had been a friend of Sam's a long time ago. She had actually killed her mom to save Sam. Briefly, she engaged in her monster nature in order to help her son, who was sick. However, she said that she wouldn't do it anymore, especially now that her son was healthy.

After promising Sam that he would leave Amy alone, Dean killed her. Worse yet, he killed her in front of her son. We're still waiting for the son to come back for Dean. Maybe that will happen later in Season 15.

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