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2. Angels

Supernatural - Evil Angel made by Asmothesly's channel
Gadreel, Ezekiel *Tahmoh Penikett and Jared Padalecki

Following in Castiel's footsteps, Gadreel's intentions often ended up as huge mistakes. He, like Castiel, didn't really fit the mold of angels but he didn't know how to be human either or to have a conscience until later, when it was already too late. He survived many years in Heaven's prison and against the torture. For some reason, neither sounds like a stroll on a park. His strong presence was mostly made real by none other than the two marvelous actors who played him. As his character grew, he knew the error of his ways in the end and he decided to pay the ultimate price for it.
"I sat in this hole for thousands of years thinking of nothing but redemption, of reclaiming my good name. I thought of nobody, no cause other than my own... The only thing that matters in the end is the mission: protecting those who would not and cannot protect themselves. The humans. None of us is bigger than that, we will not let our fears, our self-absorption prevent us from seeing it through. Not anymore... Move to the other side of your cell Castiel, and keep your head down. When they say my name, perhaps I won't just be the one who let the Serpent in, perhaps I will be known as one of the many that gave Heaven a second chance." – 9.23 Do You Believe in Miracles?
Known status: Deceased
Seen: 9.01 I Think I'm Gonna Like It Here, 9.02 Devil May Care (as Sam), 9.03 I'm No Angel (as Sam), 9.04 Slumber Party (as Sam), 9.05 Dog Dean Afternoon (as Sam), 9.08 Rock and a Hard Place (as Sam), 9.09 Holy Terror (as Sam), 9.10 Road Trip, 9.18 Meta Fiction, 9.21 King of the Damned, 9.22 Stairway to Heaven and 9.23 Do You Believe in Miracles?
Gabriel, Trickster, Loki *Richard Speight Jr.

At first, he was the Trickster and then he was revealed to be the archangel Gabriel. Even though his plan was fun and games, it doesn't mean that those games were not the worst to those who were afflicted by them. Gabriel wanted to teach people a lesson and Sam and Dean were no different. It would be great to find out who his vessel was. In the end, Gabriel lost his strength when he went full out against his brother even if it was the right thing to do. His tricks were over in that moment but people still have hope that he will return.
"Shut your cake hole. You don't know anything about my family. I love my Father, my brothers. Love them. But watching them turn on each other? Tear at each other's throats? I couldn't bear it! Okay? So I left. And now it's happening all over again." – Gabriel, 5.08 Changing Channels
Known status: Deceased
Seen: As The Trickster: 2.15 Tall Tales, 3.11 Mystery Spot and As Gabriel: 5.08 Changing Channels, 5.19 Hammer of the Gods, 9.18 Meta Fiction
Balthazar *Sebastian Roché

Another angel who knew how to survive but also got killed when doing the right thing. Balthazar was a rascal but he did have a heart in the right place. He valued Castiel over the Winchesters until he heard what his friend had been up to. Standing against your friend when you know he is doing a very bad thing is the ultimate sacrifice and strength. To try to show him the error of his ways is a difficult task. He did not succeed in that moment but he did try.
"The footsteps I'm following, they're yours. What you did, stopping the big plan, the prize fight. You did more than rebel. You tore up the whole script and burned the pages for all of us. It's a new era. No rules, no destiny. Just utter and complete freedom." – 6.03 The Third Man
Known status: Deceased
Seen: 6.03 The Third Man, 6.11 Appointment in Samarra, 6.15 The French Mistake, 6.17 My Heart Will Go On, 6.21 Let It Bleed and 6.22 The Man Who Knew Too Much
Michael *Matthew Cohen (5.13) and Jake Abel (5.22)

Only seen in two episodes, but he made a lasting impression both times. Being the good son and following dad's orders wasn't what made him badass. Instead, he was damned scary torching Anna just like that (and so easily), and he didn't react at all when he was torching his sister. Also, he got in John and used him in that moment shows that Michael was calculating and dangerous. He had a purpose. I am not sure I want this being out of the cage if his state of mind is what it is said to be, because I could see him be even more dangerous than Lucifer or The Darkness herself.
"Stretching back to Cain and Abel. It's in your blood, your father's blood, your family's blood." – 5.13 The Song Remains the Same
Known status: Alive-ish
Seen: 5.13 The Song Remains the Same and 5.22 Swan Song
Samandriel aka Alfie *Tyler Johnston
He was one of the good guys, trying to find Castiel and defending him even knowing Castiel had made mistakes. Samandriel lasted a long while against the torture that was inflicted upon him and still he tried to get word to Castiel and the Winchesters that the minds of the angels had been tampered with by Naomi. Unfortunately, Cas was ordered by Naomi to kill this sweet angel. The good angels don't last long now do they?

"Samandiriel: You know that there are some in Heaven that believe, despite his mistakes, that Castiel's heart was always in the right place.
Dean: Are you one of them?
Samandiriel: I think too much heart was always Castiel's problem." – 8.02 What's Up, Tiger Mommy?
Known status: Deceased
Seen: 8.02 What's Up, Tiger Mommy?, 8.07 A Little Slice of Kevin and 8.10 Torn and Frayed
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Coming soon: Parts 2 and 3 - Bad Guys, Frenemies, Humans and the Supernatural, and more!
Share in the comments your most memorable/strong men characters from Supernatural. My top choices from these categories are: Robert Steven "Bobby" Singer and Gadreel.
References:
Quotes, character information, episodes: Supernatural wiki