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- 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.
- The Omake Story "Everyone Gets Along," ...a lot of it, but mostly Erika's explanation of how she and Walker met Kadota and Shizuo imagining Izaya eating hot-pot all alone, in an Imagine Spot strangely reminiscent of "forever alone."
- Masaomi's recap of the first time he saw Anri had me cracking up.
Masaomi: "Cute smile... bitchin' boobs... ! Okay, so maybe she wasn't smiling..."
- Izaya stomping on the back of a thug, then following Mikado home with Celty making motorcycle noises all the way.
- No, Izaya was jumping up and down on the thug, laughing happily. That was most definitely funny. I couldn't stop laughing.
- When Mikado mistakenly assumes Anri was a stalker, his 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 Match Cut 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 just springs back up on his feet none for the worse, 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 Ha Ha Ha No 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 misattribution of arousal?"
Shinra: "Ah hah hah. Go die chest-first in a clay ice shaver, Izaya."
- Izaya laughing as he's stomping on a cell phone.
- "Actually, I'm trying to seduce you."
- Mikado asking out Anri:
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."
- Whenever Erika has a Yaoi Fangirl moment. She has shown a particular liking for a 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 Big "NO!".
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 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 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 Power Rangers. Made all the more hilarious when you realize that 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 11, Isaac and Miria are apparently members of the Dollars. This being 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.
- 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:
Saburo: What's with the guns?!Kadota: We're still in Japan, right?!
- There's also Saburo and Kadota having an Oh, Crap moment with armed syndicate men.
Walter: 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.
- Walker getting Wrong Genre Savvy when he thinks his idea for a technothriller novel are coming to life.
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.
- Even Walker gets Wrong Genre Savvy on a bag that contains nothing but clothes and Onigiri.
- 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 Kari Wahlgren played Amora the Enchantress of The Avengers: Earth's Mightiest Heroes.
- The Chase Scene in Episode 24 combines this with Crowning Moment of Awesome, 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 Izaya getting a shiner from Simon.
- S 2 E 4: Erika and Walker get into an argument over whether Celty counts as a Tsundere.
- 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.
- The Hilarious Outtakes are...well, quite hilarious. Steve Blum definitely takes the cake, though.
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:
- Crispin Freeman's lines are the best, mainly because he never breaks his Shizuo voice.
(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... you just wanna sleep with me, don't you?"
- Yuri Lowenthal is pretty great, too.
"In medical terms, you got fuckin' shot, son!"
- This one Lampshades one of Johnny Yong Bosch's previous roles...
Izaya (Bosch): "And why do I deserve to get my ass kicked, Shizu-chan?"
- This one comes from the first two preview videos of the dub cast—when Crispin Freeman's talking about Shizuo's fashion sense, he offhandedly notes something Johnny Yong Bosch 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...that sounds familiar...]"Johnny: "...[Izaya's parka] is really hip, especially with eskimos..."