Barry Berkman's 7 Best And 7 Worst Moments In HBO's Barry

When you're as talented of a hitman as Barry Berkman from HBO's dark comedy-drama series "Barry," leaving a life of crime behind doesn't come easy. From the pilot episode on, viewers root for Barry to escape his criminal past as he chases a new purpose found within the sanctuary of a Los Angeles acting community. While he'd never miss the mark while pursuing his target, missteps and pitfalls leave him missing the mark on his journey to redemption. 

Still, throughout Seasons 1 and 2, there's plenty of hope that there's some good left in Barry. Between his natural charm and bare-minimum good deeds, viewers are able to justify many of his worst behavior. By Season 3, the bad starts to outweigh the good as Barry's desperation for normalcy completely backfires, leaving him totally unhinged. It's time we pulled the trigger and performed an autopsy on the complexity of this character by looking back on Barry's seven best and seven worst moments.

For most of Season 1, Barry is at the mercy of the Chechen mob and is forced to pull off multiple hits on their behalf despite his attempts to get out of the business. In "Chapter Seven: Loud, Fast, and Keep Going," Barry prepares for one of his most dangerous hits yet — taking out the leader of the Bolivian mob, Cristobal. But when fellow Marines Taylor, Vaughn, and Chris tag along, Barry's plan goes out the window, leaving Taylor and Vaughn dead after driving straight into gunfire.

As far as the Chechens know, Barry is dead after his hit goes wrong, but Fuches learns the truth about his survival. Fuches turns Barry into the Chechen leader Goran in hopes of saving himself, but Goran decides to kill them both. One of Goran's henchmen, NoHo Hank, gives Barry a heads up, suggesting he run. Instead, Barry comes to Fuches' rescue and kills Goran and his men, sparing Hank's life.

This wouldn't be the last time Barry would spare Hank's life. In the Season 2 episode "Past = Present x Future Over Yesterday" Hank sets out to kill Barry after Barry fails to follow through on taking out rival mob leader Esther. Unable to get a clean shot, Barry fires back and has Hank at gunpoint. Even after attempting to murder him and putting his girlfriend Sally in danger, Barry spares Hank's life once again.

On the other hand, there were plenty of lives Barry chose not to spare. Until "Chapter Seven: Loud, Fast, and Keep Going," Barry had only killed what the show depicted as bad guys. This made it easier for viewers to sympathize with Barry, but all that changed when he pulled the trigger on one of his long-time friends. 

Chris and Barry served together in the Marines and reunite for a series of hits — but Chris doesn't pull the trigger during any of these. When a hit goes wrong, Barry forces Chris to kill so the two can survive. Afterward, a guilt-ridden Chris wants to turn himself into the police. However, Barry can't let this happen and reluctantly murders his own friend.

This is undoubtedly one of the biggest turning points for Barry in the whole show. Co-creator and star Bill Hader, who plays Barry, tells Collider, "It's when everything kind of comes together and you get to sense what the stakes were, and it's like he made this decision and you see how all these things crash together."

After Janice Moss' death in the Season 1 finale, acting teacher Gene Cousineau is devastated by the loss of his beloved girlfriend. Barry and the rest of the acting class are preparing to put on a play, but Cousineau is nowhere to be found, leaving everyone to fear they'll have to cancel the performance — and maybe the entire class. 

Barry's actions have now jeopardized his one shining light at the end of his contract-killing tunnel. Whether it's for selfish reasons or possibly because he truly cares for his fellow students and the integrity of the art, Barry convinces everyone the show must go on. He takes on the role of director, filling in for Cousineau while the teacher grieves. 

The play makes it all the way to opening night before Cousineau comes out of hiding to make an appearance on stage. Sadly, he denounces the play, saying it cannot proceed since he had no part in its development. Afterward, everyone's worst fears come true when Cousineau confirms the closure of the acting class, although this doesn't stop Barry from coming to the rescue again.

Of course, none of this would've even happened if Barry hadn't killed Janice. However, if he wanted to continue to live as a free man, he didn't really have a choice. 

After a season-long investigation of Barry's involvement in Ryan Madison's murder, Detective Janice Moss finally has Barry dead to rights. Secluded in the woods on a couples retreat with their partners Cousineau and Sally, Janice pulls her gun on Barry while everyone else sleeps soundly inside. Always two steps ahead, Barry acts fast and kills Janice with a hidden gun. He then returns to bed with a sleeping Sally and declares the end of his hitman career "starting now." 

Although Barry wants to be a good guy, it isn't going to be that easy. Bill Hader reflected on this moment in an interview with Entertainment Weekly, explaining, "I think the past always catches up. There are forces at work, and legal ramifications ... Barry is going to have to work pretty hard to make it all right."

Barry will do anything to bury the truth of his past. Before teaming up with Fuches in a career as a hitman, Barry served as a Marine, where he would come to experience taking his first life. In flashbacks, we learn about his past in the military through two lenses — one is the truth, while the other is an idealized version of events that paints Barry in a better light. 

During his deployment in Afghanistan, Barry becomes close with a fellow Marine, Albert Nguyen. While the two are on patrol investigating the murder of a donkey, they're ambushed by a hidden gunman. Albert is shot in the cheek. Barry rushes to his aid and saves his life. This would end up being one of the only noble things Barry does during his service and would later save him from death at the hands of Albert, who is revealed to have become an FBI agent assigned to investigate Barry's crimes in Season 3.

Barry's time in Afghanistan was drastically different than how he'd like to remember it and is marked by some terrible actions that could easily be interpreted as war crimes. When recounting his past to his acting class, he twists it into a story of regret. In reality, Barry and his buddies celebrated the accurate shootings carried out on three men. Later, Barry would come to realize that those three men were likely innocent. War crime number one.

There was also the time when Barry saved Albert's life. This memory doesn't end with Barry giving Albert first aid. In a fit of rage, he goes after the guy who took the shot. However, he kills the first person he sees, who turns out to be an innocent bystander. Unlike his previous killings, this action would not be celebrated by his peers. War crime number two.

Despite both of these criminal actions, Fuches is able to get Barry discharged, which marks the beginning of their hitman partnership.

There was one story that inspired the whole acting class and saved the course from permanent closure after Cousineau's heartbreak. In the premiere episode of Season 2, Barry opens up about the first time he killed someone to help show Cousineau that it's okay to share personal trauma. 

While on stage delivering his story, two other students act out the scene. Barry tells it as if he was devastated and forever traumatized by his first killing, but the truth was that he was proud of his marksmanship at the time. Moved by his fabricated story, Cousineau agrees to keep the class open and assigns the students to put on productions about their own traumas. It turns out Barry isn't the only one who has trouble facing the truth of the past. 

Sally centers her play around the time she confronted her abusive ex-husband. However, when the truth is revealed — that she left without standing up for herself — Sally struggles to go on with the play. However, Barry encourages her to tell whatever version of the story she feels comfortable with, whether it's the truth or not. Maybe the lesson here is that it's okay to lie to keep your loved ones happy, but Barry's lies will only get harder to justify from here on out.

Halfway through Season 2, while the acting class is putting on plays inspired by their personal trauma, Sally's abusive ex-husband Sam stops by to catch up with Sally. Barry joins the two for dinner and is surprised by Sally's cordial behavior, especially since he knows how the relationship ended. Sally tries to brush it off but is forced to confront her fear of standing up to her ex-husband, eventually admitting her whole play is a lie. Barry convinces her to go through with it by telling her, "You should be able to be the person you say you are."

Despite Sally's wishes for Sam not to see the play, he shows up unannounced during rehearsals where Barry confronts him. This heated exchange only sets Barry off more. He then takes it too far, showing up at Sam's hotel, gun in hand. What he doesn't know is that Sally is inside, as Sam has been trying to convince her not to do the play. When the door opens and Barry reacts, he aims his gun right at Sally. Neither Sally nor Sam notice, but Barry can't believe what he almost did.

Once Cousineau learns Barry killed Janice, there is no going back. When Cousineau's plan to kill Barry backfires, Barry is left with few options. Either he can handle Cousineau as he does with all his other problems — by killing him — or he can help Cousineau redeem his dead acting career. Barry isn't in his right mind to understand that this will do nothing for his too-far-gone relationship with Cousineau, but it's all he has.

In the Season 3 episode "limonada," Barry's first attempt to get Cousineau an acting gig fails and drives a larger wedge in Barry and Sally's relationship. With Sally's show taking off, Barry requests that Sally give Cousineau a part, but she insists casting won't allow it because of his infamous reputation of being a nightmare to work with. This causes Barry to blow up in Sally's face and forces him to find work for Cousineau elsewhere. 

Eventually, Barry lands him a small role on a TV show where Cousineau begins his redemption by making amends with people in the industry who he's treated poorly in the past. It turns out Barry's psychotic plan had some positives after all, but this still wouldn't stop his actions from coming to a disastrous head.

Although Barry had a plan to redeem Cousineau's acting career to give him purpose once again, Barry knew the only way to keep Cousineau quiet was to threaten his family. As if his killing streak wasn't bad enough, threatening Cousineau's son Leo and young grandson Gordon ends up being an all-time low for Barry.

Cousineau's son Leo is introduced in the Season 2 episode "The Power of No." We learn about their rocky relationship and how Leo believes Cousineau prioritized his acting career over his family. In Season 3, Leo and his son are living with Cousineau after Leo loses his job. After Cousineau escapes from Barry's captivity, he runs home to call the police, but Barry beats him to it. 

Leo and his son suspect nothing out of the ordinary, but Barry makes it clear that if Cousineau doesn't do what he says, he'll go after his family. The scene plays out in ways that are both eerie and uncomfortable as Barry expresses his love for Cousineau and forces him to say it back.

The Season 2 episode "ronny/lily," written and directed by co-creator and star Bill Hader, is regarded as one of the series' best episodes. It even received nominations for outstanding writing for a comedy series and outstanding directing for a comedy series at the Emmys. In an action-packed pivotal moment for Barry, he's sent to kill Detective Loach's ex-wife's new boyfriend, Ronny Proxin. Now that Loach has Barry's confession to killing Janice, he's left with no choice. 

However, at this point, Barry will do anything not to have to kill an innocent person. So when he shows up at Ronny's house decked out in all black and a red ski mask, Barry warns Ronny to pack a bag and go into hiding. This might've worked if Ronny hadn't turned out to be a Taekwondo champion. 

What ensues is an episode of impressive fight scenes, some involving a superhuman little girl who climbs trees and bites off faces. In the end, Loach is killed by Ronny, Ronny is killed by the police, and Barry gets away. At least Barry tried to resolve the situation without violence!

A side of Barry that viewers have never before seen appears in the Season 2 finale titled "berkman ﹥ block." Fuches, posing as a private detective, takes Cousineau out into the woods to show him Janice's dead body. Barry is close to catching up to them, trying to stop Fuches. However, before he can make it, Fuches whispers into Cousineau's ear: "Barry did this." 

Fuches escapes, but Barry wants revenge. He learns that Fuches is at the monastery, where Hank has set up shop. In an unstoppable rampage, Barry kills everyone in sight, including the Chechen prodigy he was training in earlier episodes. Some gang members help Fuches escape, and Barry is left to face the bloody consequences of his actions. 

While Barry is known for killing off his problems, he's never gone on a killing spree as deadly as this one. After the massacre is over, it's impossible not to see the terrifying hitman that lies beneath the surface of Barry's soft-spoken demeanor.

After Fuches sends a motocross gang connected to Taylor, the former Marine who died in Season 1, to kill Barry, viewers see a jaw-dropping motorcycle chase scene in the Season 3 episode "710N." In the end, all but one of the bikers are killed. Barry, of course, gets off scot-free in true Barry fashion. 

In the Season 3 finale, the remaining biker ambushes Barry and Sally in their home and knocks Barry unconscious. Sally is left to fend for herself and is almost killed in the process. Luckily, she gets the upper hand but takes it too far, violently killing the man. When Barry comes to, he's horrified at what's taken place, knowing that the blood on Sally's hands is ultimately his doing. 

In a tense, emotional moment, Barry takes the blame, repeating to Sally, "Barry did this." He says this not just to save her but because he genuinely understands he has brought Sally to this point of no return.

While Barry may have some good moments here and there, it's made clear time and time again that Barry is, in fact, a bad guy. He kills. He lies. He puts innocent people in danger. From the beginning, Barry is trying to balance a double life. Can he escape the thing he's good at — being a hitman — to pursue something he's not good at — acting? Even more importantly, can he change his nature? 

The answer becomes more clear with every episode. Clear, that is, to everyone except for Barry. "The whole thing, ultimately, is about hope ... the hope that things can be better for him. That there's a better life for this guy, that he can forgive himself," Hader tells Esquire. Even in Season 3, with all his secrets coming to light, Barry still lies to himself and hopes for redemption. 

His lies have done nothing but cause ruin in the lives of the people he loves most, making the possibility of Barry truly finding a new life seem further away than ever at the end of Season 3.