With Prison Break’s final episodes starting up next Friday, I thought I would look back and reminisce on the best part of this show: its villains. Not all the show’s no-do-gooders are created equal and there are some that stand out above the rest. The irony of this list is that some of these characters have switched sides of the force and you’ve probably rooted for them once or twice. But we can never forget the times when they had nothing but Michael and Lincoln’s destruction on their minds. Here’s my top 10, which by the way is most of the notable villains in the show. But who doesn’t love a good top 10 list?
Compared to the others, the third season was like the end of a loaf of bread that you don’t want to eat. But Sammy stood out as a seriously grimy villain, easily bypassing Lechero as the one to be feared in Sona. Too bad he didn’t get the memo about the falling dirt above.
This guy burned fast like one of those fake fireplace logs you buy at the supermarket. In his short time on the show, he was just about as close to a T1000 terminator as a human character could get. Just the site of the black clothes, the sunglasses and the stiff walk had viewers vicariously feeling like they were being hunted down by agents in the Matrix. But his end at the hands of Mahone was just as sweet as he was given The Sopranos treatment.
I really, really hated this lady with a passion, but she was a necessary evil and represented the first high-power villain that wanted the brothers dead. She was eventually deemed irrelevant once she stepped down from office and we found out she was doing the nasty with her own brother. Just gross man.
Lest we forget that this guy was so hard core that he actually cut off one or two of Michael’s toes. Abruzzi was, by far, one of the show’s best characters. John was well connected inside of Fox River and he was to supposed to be an integral part of the escape plan, providing an airplane to help Michael and Lincoln escape. His being the “first down” out of the Fox River 8 was an important development in Season 2, but we wish had survived a little longer.
Capable of pissing viewers off with just the simplest of smirks, Bill Kim excelled in calling shots from a distance (key word is distance). When he attempted to do things himself, he proved that he was all bark and no bite. One of the most satisfying occurrences in Season 2 is when he caught a right hook from Lincoln. Eventually, Kim got blasted in the chest by none other than Dr. Sara Tancredi. Sionara sucka!
Back in the days when Michael or Lincoln couldn’t just stroll into Company offices, this guy was depicted as an all powerful and quiet mastermind. But his untouchable status came to an end once the writers let loose with their lame attempt at a third season. In the end, he turned out to be a bland character. I only list him this high because of what he once represented - the complex and mysterious conspiracy against the brothers.
The stout jester that lived with his mom wasn’t always a cowardly lion. Bellick was charged with running interference on Michael’s escape plan the whole first season. He passed the mantle to Mahone early after the escape, but was someone to be reckoned with back in the Fox River days. He uncharacteristically met his end in Season 4, sacrificing himself so the boys could get closer to Scylla. I was sad to see him go, because Wade Williams was great as this character.
Who knew she’d rank this high on my list? Her bad acting in Season 3 and attempts to be tough were laughable, but at some point I just accepted her and she became part of the Prison Break mythos. She ended up having a soft side (for her daughter), but she was hardcore right up until the end (damn, did she die or go to prison?).
This list certainly wouldn’t be complete without one of the greatest characters in television history. A tortured soul, strangely capable of simultaneous rage and compassion, Theodore Bagwell was one mean mo-fo back in Season 1. He’s become comic relief since the escape, but always good for a ruthless killing and blatant selfishness, reminding us of why he’s a convict in the first place. I’ve never really felt like T-Bag was THE main Prison Break villain, but he’s probably done the most evil out of all the characters, thus his high ranking on the list.
This guy was scary. All business and his gun never missed - Kellerman is one of the reason’s why Prison Break’s first season was rock solid. He was only bested a few times (including having his chest hair ironed by Sara), but Paul was a soldier at heart. This is what made you feel for him when he ultimately met his demise (or did he?).
I know a lot of people will be pissed that I put Mahone in front of Kellerman, but Mahone was just as deadly as Agent Paul, plus he was more interesting of a character. What better motivation to hunt down 8 convicts than for the safety of his own family? I’ll never forget those moments during Season 2 when Mahone and Scofield met face to face - a “hunter and the hunted” situation at its best. He’s still a conflicted character (and brilliantly acting by William Fichtner), it will be interested to see how he ends up. I’m rooting for a happy ending.
There you have it. I’m sure everybody has their own version of the top villains, especially 1-5, - that’s why we have a comments section below!

















yeah i think T-Bag should be number one too. icky feelings is right, he is well written and well acted. definitely one of the better TV villains. I think Abruzzi should be way better ranked than Gretchen though, she would be number Ten on my list but I know some people who really liked her.
I also want to say that I think the show really lost its touch by the end of season 2 and I’m really bored with what it has become since. It was better when the writers did not try to explain “The Company” and it was left as an abstract metaphor for force, power and and government, like “Empire” in Coetzee’s Waiting for the Barbarians.
One of my favourite shows though, still.
T-bag is the main villain hence why he has remained so involved in the plot. Everyone has also forgotten donald self? He betrayed everyone after all making him an unlikely villain!
Can’t wait for the Gretchen spinoff hope it happens or at the very least we get to see the two hours they shot of her in Prison
I have worked in prisons before and T-Bag encompasses every icky feeling I ever had with some inmates. Some people just put off an evil vibe and the T-Bag character had that down pat!!
T-BAG - he might not be the main villain, but he’s been the best villain on the show. Just think of all the crazy stuff he’s done and NOT at the command of The Company.
PRetty good list - Mahone is definitely my number 1 too. Please move Gretchen to number 10 though
Kellerman was the best villain… and I’m still holding out hope that he returns!!