13 “Not making a decision is a big decision.”

Season 7, Episode 1 (2016)

Many of the best Negan quotes came in the season six finale and the season seven premiere. These came from the moments where Negan made his violent introduction by brutally murdering two members of Rick’s group and trying to bully the survivors into complete submission. Having bludgeoned Glenn (Steven Yeun) and Abraham (Michael Cudlitz) to death, Negan tries to further impose his will on Rick by offering him an impossible ultimatum: cut off his son’s arm or everyone in the group will be killed.

As Rick is reduced to a sobbing mess and finds himself incapable of making a conscious choice, Negan assures Rick that his indecision is of no small significance. In a merciless world where efficiency and action were everything, the moment highlighted how great a threat the Survivors were to the group, and the quote emphasized that Negan was by far the most formidable foe Rick’s group had faced.– Ryan Heffernan

12 “Punishment – can’t do anything without that. Punishment is how we built everything we have.”

Season 7, Episode 16 (2017)

The Walking Dead was often at its best when it was exploring human morality and philosophies in an intense kill-or-be-killed environment. Throughout the show, this focus presented many intriguing ideas on leadership, from heroes like Rick Grimes (Andrew Lincoln) and Maggie Greene (Lauren Cohan) to antagonists like the Governor (David Morrisey); and Negan stands as an underrated figure in this regard.

In such a demanding world, Negan opted to govern through fear, a belief he all but confirms when he explains his plans to Sasha (Sonequa Martin-Green) about how he will make Rick’s group submit to his rule. While many of Negan’s greatest quotes are wry insults or striking threats, this jarring revelation of his perspective on the world and his people offered great insight into his domineering mindset and his views on leadership. – Ryan Heffernan

11 “This is Lucille, and she is awesome.”

Season 6, Episode 16 (2016)

While his eccentric charisma, his complete immorality, and his penchant for extreme violence have gone a long way to defining him, there is nothing that has contributed to Negan’s iconic standing quite like his beloved barbed-wire shrouded baseball bat, Lucille (an iconic weapon from TWD). Therefore, it was only right that Lucille got the introduction she deserved when Negan made his long-awaited first appearance in the final episode of The Walking Dead’s sixth season.

As part of his monologuing introduction to Rick’s group who are helplessly held before Negan and his mob of foot soldiers, the famous villain takes great delight in tormenting the show’s heroes. Morgan’s delivery of the line “this is Lucille, and she is awesome” perfectly established the twisted nature of the character as being both infectiously fun and incredibly intimidating. – Ryan Heffernan

10 “I can’t be the only one to notice that you got a fat lady in charge of keeping track of the rations, can I?”

Season 7, Episode 4 (2016)

While it can be deemed problematic or inappropriate to target someone’s weight as the punchline of a joke, such comments can be used exceptionally well when it comes to characterization, particularly surrounding crude villains. As the crudest of crude villains, it should come as no surprise that Negan would be the person to resort to such a quip while touring Alexandria in the fourth episode of season seven, “Service.”

In the midst of his exploration of Alexandria, he stumbles across the community’s supplies and Olivia (Ann Mahoney), the woman in charge of overseeing the distribution of food and weaponry. While Negan’s remark was undoubtedly in poor taste, it highlighted the relentless abuse he enjoyed subjecting people to. On a positive note though, Mahoney stated that working on set with Jeffrey Dean Morgan was a delight and that showrunner Scott Gimple was eager to ensure she felt comfortable.

9 “Is that you, Rick? Underneath all that man bush? S**t, I would not have messed with that guy!”

Season 7, Episode 4 (2016)

Negan has always been a source of both cruel comedy and scathing intensity on The Walking Dead, sometimes even managing to do both at the same time while tormenting those he wants to reign over. A perfect example of this comes in “Service” when, while venturing throughout Alexandria, he comes across a video of Rick being interviewed by Deanna (Tovah Feldshuh) which was taken when Rick’s group first arrived.

With the open wound of Negan’s attack on the group – and his gruesome murder of Glenn and Abraham – still raw, his jibe about Rick’s intimidating, bearded appearance wasn’t just a funny one-liner but a psychological twisting of the knife, musing that he may not have bothered Rick’s companions had he been so fearsome. The mean-spirited mockery is Negan to a tee, and was perfectly delivered by Morgan with his trademark enthusiasm.

8 “I never know exactly which eye I’m supposed to look at.”

Season 9, Episode 8 (2018)

Across his tenure in the show, Negan has formed a habit of targeting the ailments or looks of other survivors under the guise of playful yet cutting mockery. Always delivered with an underlining, belittling punch, his jabs were plentiful with a select few standing out. Among them was his teasing of Father Gabriel’s (Seth Gilliam) blind eye in the season nine episode “Evolution.”

While being held in captivity, Negan is visited by Father Gabriel who tries to comfort the prisoner only for his good-natured efforts to be met with snide, antagonistic remarks. While the quote was another funny example of Negan’s knack for mean-spirited humor, it was laced with an even more cynical tone when it is remembered that Gabriel contracted the infection that would blind him while coating himself in Walker guts with Negan to escape a herd.

7 “You do the same damn stink eye as you dad – except it’s only half as good, cause, you know, you’re missing one eye.”

Season 7, Episode 7 (2016)

Out of everyone in Rick’s group, it was with Carl (Chandler Riggs) that Negan developed the most interesting relationship. While the mockery and mind games tended to flow both ways between the two, there was always something about Carl that made Negan view him in such high regard. It may be the fact that Carl never backed down against him or whether it was just because the kid had become a badass survivor on TWD.

However, this didn’t make Carl impervious to Negan’s insults, with his missing eye a target of the villain when he wanted to deliver a wry quip. In the season seven episode “Sing Me a Song,” Negan is giving Carl a tour of his base, Sanctuary, a facility Carl disapproves of. His scowl prompts Negan to tease “You do the same damn stink eye as your dad – except it’s only half as good, cause, you know, you’re missing one eye.”

6 “I thought we were having a moment, you little a**hole!”

Season 8, Episode 8 (2017)

Despite his well-hidden love for Carl that he always kept deep down, Negan still had his moments of frustration with the teen. One of the most memorable of which came in the season eight episode “How It’s Gotta Be” when Carl hinted at opening up to Negan to execute a ruse, one which left the beloved villain saying one of the funniest lines in the series.

With Negan’s arrival at Alexandria, his demands of surrender are interrupted when Carl meets with him and seemingly has a heart-to-heart to create a distraction that will allow the people of Alexandria to escape into the sewers. When he realizes he’s been had, Negan blurts out “was that just a play? I thought we were having a moment, you little a**hole!”

5 “Sucks, don’t it? The moment you realize you don’t know s**t.”

Season 6, Episode 16 (2016)

“S**t” was probably the most prolific word in Negan’s vocabulary, especially in the early days of his tenure on the show when he preoccupied himself with terrorizing Alexandria. Sometimes it was used in a wise guy, smart-alec manner, but other times he used it with a bleak earnestness to impart words of wisdom to friend and foe alike.

This was the case in his very first moments when he set to antagonizing Rick’s group having cut them off on the road in the infamous season six finale, one of the scariest The Walking Dead moments. As he stands over the group, taunting them with a terrifying glee as they kneel desperately before him, he looks down at Rick with his signature smirk and says “sucks, don’t it? The moment you realize you don’t know s**t.”

4 “You’re not saving this world, Rick. You’re just getting it ready for me.”

Season 9, Episode 2 (2018)

While Negan was always a great source for a hilariously twisted insult, it is sometimes forgotten how utterly terrifying he could be when he got serious and spiteful. Early in season nine, Negan hadn’t quite started his redemption arc and the series was still eager to present him as a villain at large. At the end of the season’s second episode, “The Bridge,” it is revealed that Negan is being held captive in Alexandria, with Rick telling him about the status of the rebuilding communities.

When it is revealed to be Negan who Rick is talking to, his updates take on more of a taunting tone, with Rick emphasizing that people are thriving free from Negan’s oppressive rule. However, Negan gets the last laugh, stoking Rick’s ire by mentioning Carl before claiming “you’re not saving this world, Rick. You’re just getting it ready for me.” – Hannah Saab

3 “It’s gonna be pee-pee pants city here real soon.”

Season 6, Episode 16 (2016)

After episode upon episode of build-up to Negan’s eventual reveal, the season six finale introduced the character in all his promised glory, establishing him as an eccentric and volatile figure with a love for intimidating people through humor. With Rick’s group brought to their knees before the might of The Survivors, Negan lets the Negan-isms fly fast and loose as he takes great pleasure in tormenting his desperate victims with what he has planned for them (some of the most painful deaths in TWD).

While towering over them, Lucille firmly in hand, Negan spews forth the line “”we pissing our pants yet? Oh boy, do I have a feeling we’re getting close. It’s gonna be pee-pee pants city here real soon.” Audiences didn’t know whether to laugh or panic as the quip was delivered by Morgan with such effervescence that the character became instantly iconic.

2 “No one ever thinks that they are the evil one.”

Season 9, Episode 16 (2019)

Heroism and villainy are but a matter of perspective. That was the sentiment Negan came to embody and a fact fans often pondered at times when Rick’s group was forced to do unpleasant things in order to survive. The idea was quite succinctly stated in The Walking Dead‘s season nine finale “The Storm” when, having saved Judith’s life, Michonne (Danai Gurrira) approaches a wounded Negan to thank him for his uncharacteristic heroism.

As the two converse, they find something of a compromised common ground over their shared experience as leaders, something which leads Michonne to say “facing evil brings good people together.” While the line can be viewed as a subtle dig at Negan, his retort, “no one ever thinks that they’re the evil one,” did shed some light on his past actions and the lengths people will go to in order to triumph over their enemies.

1 “Lucille is thirsty… She is a vampire bat!”

Season 7, Episode 1 (2016)

Picking up immediately where the season six finale finished, the season seven premiere “The Day Will Come When You Won’t Be” opened with Negan brutally beating Abraham to death with his bat before abruptly deciding to kill Glenn as well. The graphic deaths were incredibly upsetting, not only for their narrative impact, but for their intense imagery as well, but that didn’t stop Negan from telling an ill-timed joke for his own amusement.

It was immediately after he bludgeoned Glenn, before Maggie and the rest of the group no less, that Negan quipped off his bloodied bat that “Lucille is thirsty… She is a vampire bat!” While Negan did become something of a redeemed protagonist as the show went on, this striking introduction, rife with sadism and menace, marked him as a horrifying, disdainful foe from the outset.