Thanks to earnest acting from Chris Pratt and the perfect balance of heart and humor struck by Guardians of the Galaxy writer-director James Gunn, Peter Quill is one of the most lovable, endearing, and strong-willed characters in the Marvel Cinematic Universe.

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Since his mother died when he was eight, his biological father turned out to be a genocidal planet who killed her, and his adoptive father sacrificed himself to save him, Quill has had one of the most tragic arcs in the MCU. But he’s also one of the franchise’s most hysterical characters. Here are Star-Lord’s five funniest (and five most heartbreaking) quotes in the MCU.

Funniest: “Oh, I’m Sorry. I Don’t Know How This Machine Works.”

When Peter Quill is locked up in the Kyln with the other would-be Guardians in the first Guardians of the Galaxy movie, he walks out in front of the height chart for his mugshot under the watchful eyes of the guards and does the hand-crank middle-finger trick.

He adds a little bit of extra sting to the schtick when he pretends to be surprised by the extension of his middle finger and tells them, “Oh, I’m sorry. I don’t know how this machine works.”

Most Heartbreaking: “You Shouldn’t Have Killed My Mom And Squished My Walkman!”

Ego and Peter clash in Guardians of the Galaxy Vol 2

Peter Quill realized the sinister motivations of his father, Ego, when it was revealed that Ego gave Quill’s mother the brain tumor that ultimately killed her. And to top it all off, he also crushed Quill’s prized Walkman — which his mother gave him as a gift — in his hands.

Right before the climactic battle, Quill tells Ego, “You shouldn’t have killed my mom and squished my Walkman!” The soundtrack is matched perfectly to this scene, as the emotionally charged opening bars of Fleetwood Mac’s “The Chain” play, leading into the final showdown between the hero and villain.

Funniest: “Dude, Don’t Call Us Plucky. We Don’t Know What It Means.”

Star-Lord insults Iron Man on Titan

A one-sentence summary of Guardians of the Galaxy might refer to the titular team as a “plucky band of intergalactic mercenaries.” However, as we learned in Avengers: Infinity War, the Guardians don’t actually know what the word “plucky” means.

When Tony Stark proposes a plan to ambush Thanos on Titan, he mentions that they can’t take down the Mad Titan with just but “a plucky attitude,” and Peter Quill cracks, “Dude, don’t call us plucky. We don’t know what it means.”

Most Heartbreaking: “Sometimes, The Thing You’re Searching For Your Whole Life Is Right There By Your Side All Along.”

Chris Pratt as Star-Lord and Zoe Saldana as Gamora in Guardians of the Galaxy

If there’s a take-home message in Guardians of the Galaxy Vol. 2, it’s this. Peter Quill uses it to refer to the fact that he spent his whole life searching for his biological father and, through an incredible adventure, he learned that he knew his true father all along: Yondu.

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It could also refer to both Quill and Gamora’s search for love, and how they found it with each other. They’re both damaged people with tragic backgrounds, and they’ve helped each other to deal with their respective traumas. These are wise words to live by: “Sometimes, the thing you’re searching for your whole life is right there by your side all along.”

Funniest: “I’m Gonna Make Some Weird S***!”

Peter Quill is ecstatic to learn that he’s only half-human in Guardians of the Galaxy Vol. 2, and that his other half is made up of alien god DNA that grants him immortality and (in Palpatine’s voice) unlimited power.

As Ego explains to Quill that he will be able to live forever and conjure up anything within the bounds of his imagination as long as he can tap into “the light,” Quill hilariously exclaims, “I’m gonna make some weird sh*t!”

Most Heartbreaking: “I Told You To Go Right!”

Quill points his blaster at Gamora and Thanos in Avengers Infinity War

The romantic subplot in the Guardians of the Galaxy movies didn’t fall into the unrealistic pitfalls of the usual love stories in blockbusters. Peter Quill actually had to grow up and become a better person before Gamora entered a relationship with him. They don’t say, “I love you,” until Avengers: Infinity War, when Gamora forces Quill to keep the promise he made to kill her if Thanos ever captured her.

As he accepts what he has to do, Quill tearfully laments the fact that it could’ve been avoided if she followed his plan — “I told you to go right!” — even though Thanos probably would’ve gotten to her anyway. It turns out to be futile, too, as the Mad Titan uses the Reality Stone to turn Quill’s blaster fire into bubbles.

Funniest: “If I Had A Blacklight, It’d Look Like A Jackson Pollock Painting.”

Star-Lord flying the Milano in Guardians of the Galaxy

This is the kind of shockingly dirty joke that you don’t usually hear in a movie backed by Disney. According to James Gunn, viewers weren’t the only ones surprised that the Mouse House signed off on this line making it to the final cut.

Gunn explained, “The Jackson Pollock line was something I said on set and asked Chris [Pratt] to say. We only filmed it one time. People thought we were wasting time on set, because nothing that dirty would ever make it into the film.”

Most Heartbreaking: “Oh, Man...”

Some of Chris Pratt’s finest acting in the role of Peter Quill comes when he’s crushed and defeated and accepts that he hasn’t triumphed over the bad guys despite his best efforts. This is seen as he drops to his knees while Ego’s planet implodes around him, right before he’s saved by Yondu.

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And it’s most prevalent as he turns to dust at the end of Avengers: Infinity War. He watches most of the other Guardians turn to dust following Thanos’ unprecedented victory, and then notices that he is turning to dust himself and simply says, “Oh, man...”

Funniest: “He’s Trying To Copy Me!”

Star-Lord jealously watches as Thor talks to Gamora

The banter shared by Peter Quill and Thor is always hysterical. When the God of Thunder comes aboard the Benatar in Avengers: Infinity War, Quill is immediately threatened by him. The other Guardians gush over Thor, including Gamora, which makes Quill jealous.

As Thor attempts to take the Benatar’s escape pod, Quill tells him, “You shall not be taking our pod today, sir,” in a fake British accent with a deeper tone than usual. Thor catches on that Quill is imitating him, but Quill plays it off like Thor is imitating him.

Most Heartbreaking: “I Had A Pretty Cool Dad.”

Few Marvel fans can make it through Peter Quill’s eulogy at Yondu’s funeral without tearing up. He explains that he used to tell the other kids that his dad was David Hasselhoff because he didn’t know his biological father, and the dad he ended up with wasn’t too dissimilar to Hasselhoff after all.

Yondu’s sacrifice, paired with Quill’s biological father Ego turning out to be a psychotic mass murderer, made Star-Lord realize that he knew his real father all along. The guy who raised him wasn’t perfect, but he tried his best.

NEXT: Tony Stark's 5 Funniest (& 5 Most Heartbreaking) Quotes In The MCU