* Apparently, Celty is afraid of aliens.
--> '''Celty:''' "What if it was a space alien?!"\\
'''Shinra:''' "...Celty...is this where I'm supposed to laugh?"
** It's safe to say anytime that Shingen is onscreen, there is bound to be hilarity. Other moments include Shinra accidentally (he thought it was Celty) walking on him in the shower. As well as the whole argument where Shinra and Celty are trying to get Shingen's blessing.

[[folder:Light Novel]]

* [[http://anni-fiesta.livejournal.com/32129.html The Omake Story]] "Everyone Gets Along," ...a lot of it, but mostly [[{{BlatantLies}} Erika's explanation of how she and Walker met Kadota]] and Shizuo imagining Izaya eating hot-pot all alone, in an ImagineSpot strangely reminiscent of "[[http://knowyourmeme.com/memes/forever-alone forever alone]]."


* Masaomi's recap of the first time he saw Anri.
-->'''Masaomi:''' "Cute smile... bitchin' boobs... ! Okay, so maybe she wasn't smiling..."
* Izaya jumping up and down on the back of a thug, then following Mikado home with Celty making ''motorcycle noises'' all the way.
* When Mikado mistakenly assumes Anri was a stalker, his [[ImagineSpot Internal Puppet Show]] plays out the possible scenarios, including a Yandere Anri coming after him with a knife--''"I love you!"'', lighting up his home--''"Fire!"'', and kidnapping his parents.
* Episode 3: "Sooo... let's go pick up chicks!" Already one of Masaomi's funniest non-sequiturs, immediately followed by a MatchCut to him attempting to pick up girls. Adult women. From their point of view.
** Also in this episode, Shizuo's punch sends a gang member flying through the air, and ''his clothes fly off!''
* In Episode 3, out of nowhere, a trash can flies from off-screen to hit Izaya in the face, sending him sprawling on the ground. Kida cringes but Mikado just stares.
--> ''"Why? Why? Why did a trash can... ?"''
** ...and then, as Izaya [[MajorInjuryUnderreaction just springs back up on his feet none for the worse]], [[IncomingHam enter Shizuo]].
* Shinra walked into a shower. He was expecting Celty. His face was of utter glee. Then he sees his father in the shower.
-->'''Celty:''' "What happened?:
-->'''Shinra:''' "I have seen the face of hell..."
* Shinra's HaHaHaNo moment after Izaya trolls him by handing his cellphone number to the police.
-->'''Izaya:''' "How was it? Gave you quite the adrenaline shot, didn't it? Did you and Celty just grow to love each other even more due to the [[http://en.wikipedia.org/wiki/Misattribution_of_arousal misattribution of arousal?]]"\\
'''Shinra:''' "Ah hah hah. Go die chest-first in a clay ice shaver, Izaya."
* Izaya [[http://www.youtube.com/watch?v=2tAZxxUiQIY laughing as he's stomping on a cell phone]].
* "Actually, I'm trying to seduce you."
** And she looks so hot doing it!
* Whenever Erika has a YaoiFangirl moment. She has shown a particular liking for a [[FoeYay Shizuo/Izaya]] pairing as shown when Shizuo says he's going to Izaya's place (to murder him...) and she sparkles with blush stickers saying that he must love him. Everyone (Celty and Kadota's group) cuts her off with a BigNo.
--> '''Shizuo:''' "I'm off to Shinjuku to murder Izaya."
--> '''Erika:''' "Hey, hey! Shizu-chan's definitely in love with Izaya. Two guys... Like BL!"
--> '''Celty, Togusa, Dotachin and Walker:''' "No!"
* Simon trying to get his Russia Sushi signs in front of the TV cameras.
* Masaomi comparing things to polygamy and voicing his approval. It's ridiculous enough by itself, but then Mikado just says, Ployga-what?
* "Call me 'daddy!'" (Holds up sign).
** "Why is there [[ImprovisedWeapon a street sign]] in the middle of the road?"
* Really, all of Episode 6 is a CMOF, from the kidnappers spilling chloroform on themselves to Togusa's face at the concert to Kadota [[DidIJustSayThatOutLoud forgetting to keep his internal monologue internal from Erika and Walker]] to "Sparkling naked~!" to Shizuo throwing a plastic elephant at Izaya...and also, the dog.
* From Episode 7: "Shizuo is acting like he's going through puberty?" Oh Simon...
* In Episode 7, Shizuo gets fired from one of his jobs by beating up the Franchise/PowerRangers. Made all the more hilarious when you realize that [[Creator/JohnnyYongBosch Izaya's voice actor]] was a former Power Ranger.
* Episode 7: Shizuo's remark about how much Shinra's changed after Raira.
-->'''Shizuo''': "This idiot -- well he's the same."
* In Episode 10, Mikado's brain goes into overdrive when he starts thinking Anri is a StalkerWithACrush. On the flip side, if she's cute then maybe it's okay to be stalked. But then, Mikado starts to imagine puppet show scenarios where Anri goes {{Yandere}}. Scene 1, stabbing him with a knife. Scene 2, burning his house down. Scene 3, kidnapping his parents.
** What follows after that is Mikado and Anri meeting the ringleader of Ganguros and her second boyfriend, looking to get payback for her cellphone getting stomped by Izaya in episode 3. Mikado's [[OhCrap face]] [[BlueWithShock upon remembering what happened]] sells it.
*** In addition, the exchange that follows:
--> '''Ringleader's Boyfriend''': So, you're friends with the guy who broke my girlfriend's cell?
--> '''Mikado''': Well, I wouldn't really call him my friend...
--> '''Ringleader's Boyfriend''': Then what is he? Your [[TeenPregnancy parent?!]] A cosigner[[note]]basically, a person paying off someone else's debt[[/note]]?! Huh?!
--> '''Mikado''': I think your assumptions are a tad biased...
** Celty's attempt at lying to Mikado about [[spoiler:Mika]] being her lost relative. Mikado sees right through it, and again, his face sells it.
--> '''Celty''': I'm looking for a girl. She's a relative of mine, who's gone missing. I found her yesterday, but then she ran away for some reason.
--> '''Mikado''': It's a terrible liar.
* In Episode 11, [[spoiler:[[LightNovel/{{Baccano}} Isaac and Miria]] are apparently members of the Dollars]]. This being [[spoiler:Isaac and Miria]], even a minor cameo manages to be amusing.
* In the epilogue of Episode 12, Mikado works up the courage to ask Anri out, finds Kida trying to flirt with her, and, finally fed up with it, lays him out on the ground with a kick. Here's how it goes down, as narrated by Celty:
-->'''Celty:''' "In 30 seconds, the boy will find the girl. In 35 seconds, the boy will discover his best friend hitting on the girl. In 45 seconds, the boy will kick the crap outta him. In 74 seconds, the girl will reject the boy's offer to get coffee. And in 78 seconds, that girl will ask the boy to have lunch with her on the roof."
* Episode 12.5, Izaya tells some guys that Shizuo stole something from them... This goes about as well for them as you'd expect, and as they're flying out the window in plain view of everyone, Izaya remarks:
--> [[DevilInPlainSight "You know, it's kinda scary how much people trust me."]]
** There's also Saburo and Kadota having an OhCrap moment with armed syndicate men.
---> '''Saburo''': What's with the guns?!
---> '''Kadota''': We're still in Japan, right?!
*** Walker getting WrongGenreSavvy when he thinks his idea for a technothriller novel are coming to life.
----> '''Walker''': What is going on? Is the good lord ripping off my own novel? Do they have mind-reading devices too? Everything I wrote is being played out right before me.
*** Even Walker gets WrongGenreSavvy on a bag that contains nothing [[spoiler:but clothes and Onigiri]].
-----> '''Walker''': [The bag] probably contains an ultimate built to destroy the entire human race. ''(Kadota opens bag)'' No! Don't open it! It's going to blow up!
-----> '''Kadota''': ''(Surprised that he found the contents to be harmless.)''
-----> '''Walker''': Or maybe not.
-----> '''Kadota''': Guess that alien was going on vacation.
** All of the English spoken in this episode. It's just all so terrible.
* In Episode 14, Shingen is trying to cheapskate his way out of paying Celty for transporting him. Celty uses her darkness... stuff to wrap Shingen's neck in thorny vines.
--> '''Shingen:''' "I was just testing you, Celty-kun. If you release me now--Ow ow ow they're poking me! Those pointy shadow things pricked me a little! Shinra! I am in grave danger here!" ''(Struggling)'' "If you are my son, you should know what you need to do!"
--> '''Shinra:''' "Of course I do" ''(Pickpockets Shingen's wallet and throws it to Celty.)''
** And right after it, as Shinra declares that he would be happy if Celty stole his soul, she blows a heart-shape from her head smoke.
* Somewhere in the series, Shinra, calls Celty "Enchantress". Take note, Celty's English voice actress Creator/KariWahlgren played Amora the Enchantress of ''WesternAnimation/TheAvengersEarthsMightiestHeroes''.
* The ChaseScene in Episode 24 combines this with CrowningMomentOfAwesome, mostly because Horada and his lackeys are ''completely'' out of their league against Shizuo and Celty, and their faces when they realize it...! Celty "seducing" Shinra later on is also pretty dang hilarious.
* Episode 25 is pretty much 30 minutes of Crowning Moment of Hilarious Awesome. From Yuhei's TV segments, Shinra being Shinra, and Simon's sushi hocking to the parkour fight, Erika being Erika and the twins being the twins, it's just, to quote Izaya, "fun." It's funny when the fighting starts to spread throughout Ikebukuro just 'cause of Izaya and Shizuo trying to fight with each other.
** The final episode has [[spoiler:Izaya getting a shiner from Simon.]]
* Season 2 Episode 4: Erika and Walker get into an [[LampshadeHanging argument]] over whether Celty counts as a {{Tsundere}}.
* Shizuo's expression after Varona stabs him in the last episode is like he's just wondering if she is an idiot. Heck just Shizuo in that episode is just so hilarious that I ended up rewatching it several times.
* If you're into BlackComedy, Yodogiri tells Izaya on the phone that he needs to take a break. Said break consists of him being stabbed with a knife on the streets of Ikebukuro.
* When Vorona asks Shizuo on what kind of martial art allows you to flick someone without exerting a lot of efforts, Shizuo tells her that it's from the same martial arts that teaches you to smack people.
* In Season 2 Episode 25, "Even A Chance Acquaintance is Decreed by Fate", continuous hilarity occurs when Celty comes back to her and Shinra's apartment to find ''everybody'' crammed in there.
** Mika and Namie both fawning over Seiji while slinging insults at each other.
** When Celty criticizes Namie for her amorality, Namie reminds Celty that Shinra had a part in [[spoiler:hiding her head]], to which Celty says Shinra has been on the receiving end of her fury. "Please, I'm sure you just smacked him once, then messed around in the most disgusting way. Just like a beast." Celty shoots a cloud of shadow out of her neck like a volcano and immediately types, "HOW DID YOU KNOW!?" Shinra, with BlushStickers, says "That's so rude, calling her a beast! [[AggressiveSubmissive At night, Celty's actually like a little bunny]]--" at which point Celty shuts him up by gagging him with shadows, ready to die with embarrassment that their sex life is being discussed in front of everyone they know. And Shingen, still being held in mid air by her coils, says "[[DirtyOldMan Just what did you and my son do at night? Please elaborate!]]"
** Celty worries about what "That pervert" Izaya is doing with her head, to which Shinra assures her that Izaya is only interested in humans. "I'm sure he's treating your head like a mere ball, or, at most an expensive vase or something". Celty says he isn't helping her at all!
* When [[http://herskyofdiamonds.tumblr.com/post/101357980275/orihara-kururi-orihara-mairu-then-have-you the twins meet up with Shizuo.]]
* In [=S2E29=], Shooter appears before Shizuo [[spoiler:while following Celty through the city in her primal form,]] stopping to get his help. Beckoning him to get on, Shizuo replies that he's never ridden a horse before. The horse proceeds to turn into bike-form... only for Shizuo to say that he doesn't have a motorcycle license. Cue Shooter absorbing the [[spoiler:bicycle that Shizuo got from a bunch of [[BrattyHalfPint Bratty Half-Pints]]]] trying to be tough on him earlier, with any sounds of whinnies replaced with a [[spoiler:bicycle bell]]. Did we mention that Shooter still rockets around at the same speed as he usually does?
* Walker learns about Saika and immediately starts fangasming over the potential of becoming superhuman, but the moment he learns that the cost of it would be having to love humans (in other words, 3D people). He turns it down, loving 2D too much.

* In Chapter 10 of the manga, there's a comedic page featuring Harima and her six phases of stalking. Let's just say it goes from Harima's victim showing natural human kindness to Harima following the poor guy on a family vacation.[[http://www.mangareader.net/1318-48901-10/durarara/chapter-10.html]]



* The HilariousOuttakes are...well, [[ExactlyWhatItSaysOnTheTin quite hilarious]]. Creator/SteveBlum definitely takes the cake, though.
--> '''Kadota (Creator/SteveBlum):''' (Hands Mikado a [[SubliminalAdvertising thinly-veiled]] can of Red Bull) "Like roofies?"
--> '''Mikado:''' "Oh, thank you."
--> '''Kadota:''' "You know this means we're going steady now."
** Kadota: "She can see into your bedroom, you know. She knows you're wearing her panties again."
** So much VA {{Lampshading}}. Particularly:
---> '''Horada (Creator/KyleHebert):''' "'''''CAUSE THIS IS THE WAY [[Anime/TengenToppaGurrenLagann TEAM GURREN]] ROLLS!!'''''"
** Creator/CrispinFreeman's lines are the best, mainly because he never breaks his Shizuo voice.
---> ''(To Izaya's sisters)'' [[Film/RobinHoodPrinceOfThieves "You at ten. You at ten-thirty. Bring a friend.]]"
---> ''(To Izaya, on the phone)'' "Let me guess, he just ''happened'' to live in Ikebukuro, and he just ''happened'' to see him on TV, and that's why he came by. And he just ''happened'' to bring a ''knife'' with him, too! Tch... [[HoYay you just wanna sleep with me, don't you?]]"
---> ''(To Shinra on how he's still standing)'' "Cause you're Creator/YuriLowenthal, and [[Anime/{{Noein}} I'm standing in your bedroom once again]]."
** Yuri Lowenthal is pretty great, too.
---> "In medical terms, you got fuckin' ''shot'', son!"
* This one {{Lampshades}} one of Creator/JohnnyYongBosch's previous roles...
-->'''Izaya ([[Creator/JohnnyYongBosch Bosch]]):''' "And ''why'' do I deserve to get my ass kicked, Shizu-chan?"
-->'''Shizuo (Creator/CrispinFreeman):''' "Because you were a [[Franchise/PowerRangers Power Ranger]]!"
* This one comes from the [[http://www.youtube.com/watch?v=ysDntiqVX0w first two]] [[http://www.youtube.com/watch?v=M_uGC5o1rjM preview videos]] of the dub cast--when Creator/CrispinFreeman's talking about Shizuo's [[BadassInANiceSuit fashion sense]], he offhandedly notes something Creator/JohnnyYongBosch had said in ''his'' interview about Izaya. Deja vu is noted.
-->'''Crispin:''' "I mean, I don't know who this clown is who's walking around like an eskimo... (Braking tires are heard as the camera closes in on the DRRR poster behind him.) ''Wait... [[{{Flashback}} that sounds familiar]]...''"
-->'''Johnny:''' "...[Izaya's parka] is really hip, especially with eskimos..."
** Which is then [[RunningGag repeated]] in part three of the HilariousOuttakes:
--->'''Creator/CrispinFreeman''': "...Stupid eskimo."