Top 10 Best Prison Break Moments

Nothing says “brotherly love” like planning an escape from jail together. Welcome to WatchMojo.com and today we’ll be counting down our picks for the Top 10 Prison Break Moments. For this list, we’re taking a look at the most thrilling moments from this FOX drama series. Fair warning… there will be PLENTY of spoilers.
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Nothing says “brotherly love” like planning an escape from jail together. Welcome to WatchMojo.com and today we’ll be counting down our picks for the Top 10 Prison Break Moments.

For this list, we’re taking a look at the most thrilling moments from this FOX drama series. Fair warning… there will be PLENTY of spoilers.

#10: Mahone’s Rampage

“Buried”


Alexander Mahone is an FBI Special Agent hell-bent on hunting down the Fox River Eight. When he corners John Abruzzi however, the mob boss, never one to do things the easy way, opts to go out in a blaze of glory. Of course Abruzzi had previously asserted that he’d rather die than return to prison. David “Tweener” Apolskis on the other hand, peacefully surrenders upon his capture, only to have Mahone gun him down in cold blood, setting it up to look like self-defense. Suddenly, Mahone’s true motivations become much clearer. He’s not interested in simply capturing the escaped convicts - he’s their judge, jury, and executioner, as ordered by the Company.

#9: Escape Preparations

“Tonight”


You know the phrase, “whatever can go wrong, will go wrong?” That’s pretty much Michael Scofield’s escape plan in a nutshell. They hit a huge roadblock when Captain Brad Bellick discovers a hole the inmates have dug. Bellick is ultimately knocked out, but Westmoreland gets wounded in the process. As the clock winds down, Michael realizes that they need to break out that night before Bellick is missed, forcing him to solve multiple problems in very little time. These desperate escape preparations build up to a nail-biting confrontation, with Michael pulling a knife on Warden Henry Pope. TV doesn’t get much more thrilling than this.

#8: Veronica’s Death

“Manhunt”


“Prison Break” had no shortage of shocking deaths, but Veronica Donovan’s murder was perhaps the most unexpected. At the beginning of Season 2, this lawyer puts all the puzzle pieces together. Terrence Steadman is still alive, proving that Lincoln is innocent. After alerting the authorities, Veronica calls Lincoln to tell him the good news. Their relief is short-lived, however, as Company agents arrive soon after. With nowhere to run and nowhere to hide, Veronica is silenced for good. Listening on the other line, Lincoln breaks down. Her death conveys a clear message from the showrunners to their speechless viewership - in this series, no one is safe.

#7: Michael’s Tattoo Burns

“By the Skin and the Teeth”


Michael has the Fox River blueprints tattooed all over his body, providing a foolproof escape route. Even with this map, though, he can’t predict what’s waiting around every corner. After a close call, Michael returns to his cell with a severely burnt back. In order to cover their tracks, Sucre must remove Michael’s uniform, which has melted into his skin. The audience can’t help but cringe as Sucre rips off the fabric, tearing Michael’s flesh. Although the cellmates avoid getting caught, they face a new problem: a crucial part of the blueprints have been burnt off. It’s a classic “Prison Break” cliffhanger that leaves everyone asking, “how are they gonna get around this one?”

#6: Paul Switches Sides

“The Killing Box”


About halfway through the second season, Alexander Mahone finally backs the Scofield brothers into a corner. Just when it looks like they’re about to bite the bullet, an unexpected ally comes to their aid. Paul Kellerman, a Secret Service agent working for the Company, has been an enemy since day one. After shooting Mahone though, Paul explains that he’s had it with the Company and President Reynolds. He offers to become the brothers’ inside man, marking a major game changer in the series. What makes this moment even more significant is that it’s the first time Michael and Paul have come face to face, excluding a brief exchange in Season One.

#5: We’re Free

“Free”


In the original series finale, Michael attempts to rescue a pregnant Sara from prison before Jonathan Krantz (aka the General) can get to her. With freedom just out of reach, Michael decides to make the ultimate sacrifice. After a heartbreaking kiss goodbye, Sara reunites with the others and they reluctantly drive away. Sara and Lincoln later watch a DVD Michael left behind. Explaining that he was going to die from a brain tumor anyway, Michael expresses that he has no regrets and bids his loved ones a tearful farewell. Although this looked like the end of Michael Scofield, fans were given hope when Season 5 was announced years later.

#4: Mad Dash

“Hell or High Water”


Season 3 isn’t exactly a fan favorite, but at least it delivered a truly heart-pounding climax. After successfully busting out of Sona, Michael and his fellow escapees must endure a veritable obstacle course with the authorities not too far behind. This thrilling chase takes them through the jungle, down to the beach, and even underwater. Using scuba gear, they eventually make it to a rendezvous point out in the ocean, where, sadly, they discover that Sucre has failed to make it. Fortunately, McGrady's father pulls off a last minute rescue. It’s a truly thrilling and original escape without a single dull moment, nicely setting the stage for the season finale.

#3: Meeting T-Bag

“Allen”


Whether he’s acting as an ally or an adversary, Theodore "T-Bag" Bagwell is easily one of the creepiest characters in “Prison Break”. While it’s hard to single out just one T-Bag moment, our introduction to him particularly stands out. Early on, this Fox River inmate is revealed to be a murderer, pedophile, and white supremacist. Although Michael generally tries to keep to himself, his need for an allen bolt forces him to deal with Bagwell, who wastes no time trying to solicit sexual favors from our hero. Michael understandably declines, instigating one of the show’s most interesting rivalries. Talk about making a memorable first impression.

#2: Brad Bellick’s Death

“Greatness Achieved”


This one-time antagonist experiences an unlikely transformation throughout the series, going from prison guard to prisoner. Eventually joining Michael’s crew, he emerges as a friend and hero. The character most notably finds redemption with his selfless final act. During a mission to take down the Company, the team attempts to push a pipe through a tunnel. When the plan goes awry, Bellick volunteers to go into the main water conduit. The pipe is installed, but there’s no way for Bellick to escape the incoming flood, something he knew going into it. It’s a painful moment for the audience, but there’s comfort to be had in knowing that with his death, Bellick gave his life true meaning.



Before we get to our top pick, here are a few honorable mentions:



Michael’s Lockdown

“Riots, Drills and the Devil, Part 1”


Lincoln and Michael’s First Meeting

“Pilot”



Sona Orientation

“Orientación”


#1: Beginning the Escape

“Go”


Season One is an exercise in perpetually building tension. That tension peaks at the eleventh hour, when the escape officially commences. The prison break is full of twist and turns, leading the convicts to the infirmary. One at a time, they climb across a cable to a wall. Westmoreland is sadly too weak to make it, but he does reveal the location of his stolen money. Just as Michael is about to cross, the guards sound the alarms. Things only get worse when Manche accidentally breaks the cable, nearly causing Michael to fall. Lincoln saves his brother, but the chase is only beginning. Intense, unpredictable, and exceptionally paced, this is “Prison Break” at its finest.
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