As a demon (and a very powerful one at that), Crowley's whole purpose in life revolved around being the literal worst. He existed to torment the Winchesters and their various allies and, in all fairness, he did a pretty good job at being the proverbial thorn in their sides for eight seasons.
However, Crowley as a character did occasionally get worse as Supernatural went on. He made decisions that came out of nowhere and that were entirely out of character for him. He also ended up in several situations that he previously would have avoided. Even his exit was slightly worse for wear.
10 Became Addicted To Human Blood
In Season 8, Sam and Dean Winchester were on a mission to close the Gates of Hell. To do this, Sam had to complete a series of trials that were incredibly difficult and grueling. The last trial was to turn a living demon back into the human they had once been.
For the entirety of Season 8, Crowley had been after the Winchesters, so it was only fitting that he was the demon they tried to cure. They did this by giving him human blood, but Crowley eventually became addicted, which weakened his status as a villain.
9 Allied Himself With The Winchesters
Throughout its history, Supernatural has always played with the idea of introducing a "good" demon. The most notable example was Ruby, who pretended to help the Winchesters for a while, only to reveal that she had been working for Lucifer the entire time.
The next best candidate for a redeemable villain was Crowley, who was initially incredibly apathetic towards other demons. However, this did not mean he was a good person. In fact, he remained evil for the majority of the show, until he randomly decided to help Sam and Dean.
8 Sacrificed Himself To Stop Lucifer
Although Crowley might have aligned himself with Sam and Dean more frequently as the show went on, it didn't automatically mean that he had become a more selfless and kinder person. Sometimes, he only helped the brothers because he had larger plans.
However, in Season 12 (Crowley's last), Crowley went through a massive personality change. He even offered to permanently close the Gates of Hell. His death was also a self-sacrifice, an entirely selfless act, which didn't suit the character at all.
7 Became Lucifer's Prisoner
When the viewers (and Sam and Dean) first met Crowley, he was the King of the Crossroads. This basically meant that he was the head of all other crossroad demons, and that he only made deals with the humans that he deemed important enough.
After Lucifer was trapped in his Cage again, Crowley became the King of Hell, so theoretically, he should be even more powerful. But this didn't stop Lucifer from dethroning Crowley and keeping him as his pet, which just served to diminish Crowley even further.
6 Lost The Respect Of The Demons
As the King of the Crossroads, Crowley was made out to be a very powerful demon, with many other demons more scared of him than they were of the Winchesters, which was really saying something. However, this changed over time.
In fairness, it wasn't completely Crowley's fault, as the Winchesters did give him human blood which had the unfortunate side effect of making Crowley more vulnerable to emotion. But he still managed to gradually lose the respect of many demons under his rule.
5 Became The Big Bad
As brilliant a villain as Crowley was, he just wasn't bad enough to hold the title of the Big Bad, a term coined for villains who act as the main antagonist for an entire season, or longer. However, Crowley still became the main villain for Seasons 6 and 8.
This really harmed his development, as back in Season 5, Crowley presented as an unusual demon who didn't care about anything except himself. He didn't even want Lucifer to come back. Yet, in the following season, he was suddenly all about ruling over everything.
4 His Reign As The King Of Hell
When Crowley became King of Hell, fans were ecstatic as they naturally assumed that this would mean Crowley would present a serious threat to the Winchesters and the world in general. Sadly, this was not really the case, and the results were more than a little disappointing.
Crowley spent a lot of his reign trying to get his demon subjects to respect him, or better yet, fear him. However, his constant alliances with the Winchesters, as well as his lackluster idea for torturing souls in Hell meant that his reign was not a successful one.
3 Betrayed The Winchesters... A Lot
One particularly annoying aspect regarding Crowley's personality was how predictable he became in later seasons. At first, he was an enigma in the form of a demon, because he helped the Winchesters to stop Lucifer and didn't even really try to kill them.
Over time, though, Crowley developed an extremely repetitive habit. He would help Sam and Dean and align himself with them, only to betray them at a later date. It got to the point where viewers knew it was going to happen, so it wasn't fun anymore.
2 Attached To His Son, But Not His Mother
Unbelievably, Crowley's main weakness was his son, Gavin MacLeod. Gavin was brought from the past to the present just before his death, and although Crowley displayed no outward signs of affection, he did save his son from dying, potentially risking time itself.
Therefore, knowing that Crowley did care about family, deep, deep down, viewers were surprised when he didn't share the same affection for his own mother. Granted, Rowena wasn't a brilliant mom, but she and Crowley never resolved their issues before the latter's death.
1 Beaten By Abaddon
Abaddon was actually a fairly decent Big Bad during Season 9, but it always felt as though she was slightly overshadowed by the angel civil war and Metatron. Her fight with Crowley for the Ruler of Hell was intriguing, but there was one core problem: Crowley was almost beaten. He was always so calm and cool that one would be forgiven for thinking that he was unstoppable. However, Abaddon seemed to wipe the floor with him, and the only way Crowley could beat her was to have the Winchesters do his dirty work for him.
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