15 Funniest Quotes From Step Brothers

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Will Ferrell and Adam McKay are most famous for being behind some of the most iconic comedy movies ever made, including Step Brothers, which is filled with memorable quotes. Their first hit was Anchorman: The Legend of Ron Burgundy but four years later, they made another movie that is just as quotable – if not more – and while Step Brothers wasn’t ostensibly as successful as Anchorman, it has gained a huge cult following in the decade or so since its release. Like Anchorman, Step Brothers quotes continue to garner laughter even to this day.

Many were hoping over the years for a Step Brothers 2 to further open up the world of iconic Step Brothers quotes. However, that doesn’t look like it’s going to happen. Adam McKay and Will Ferrell ended their creative partnership in 2019, breaking up their company Gary Sanchez Productions. To put it simply, McKay wanted to expand the scope of his repertoire and work on more impactful projects, whereas Ferrell, did not. Either way, Step Brothers remains one of the duo’s best-known ventures with some hilarious quotes.

“God, You’re Gonna Make Me Cry. What Poem Is That From? Is That James Joyce?”

Brennan

When Brennan’s therapist Denise comes to the Catalina Wine Mixer, purely because he threatened to kill himself if she didn’t, he mistakenly takes it as a romantic gesture, leading to this entry of the hilarious Step Brothers quotes. Even though she explains her intentions in very clear terms, he just thinks she’s quoting a famous poet. Denise praises his actions at the wine mixer, calling him brave, but then amends her assertion by saying, “And I mean that in strictly the most clinical and professional sense possible, with no emotional, intimate, sexual, or any other undertones that you could possibly infer.“

Brennan basically ignores her words, but decides to spin his own meaning out of them, prompting him to ask her if what she said came from a poem. It speaks to Brennan’s own self-centeredness that Will Ferrell hilariously portrays throughout the movie. Rather than take her assertions at face value, Brennan is wholeheartedly convinced that Denise is in love with him and nothing will convince him otherwise.

“That’s So Funny, The Last Time I Heard That I Laughed So Hard I Fell Off My Dinosaur.”

Dale

When the main Step Brothers characters Brennan and Dale first meet, they’re instantly contentious with one another. At the very first dinner between the two families, Brennan barbs Dale for singing about his junk, suggesting he just drank his first beer, so Dale snaps back with one of the best Step Brothers quotes about how old his joke is.

This entry to the best Step Brothers quotes speaks volumes about the infantile natures of both Brennan and Dale. After all, they are two middle-aged men who live with, and are supported by, their parents. What makes this line so iconic is that it is without context and completely absurd coming out of John C. Reilly’s mouth.

“I Was Watching Cops.”

Brennan

One of the best-known Step Brothers quotes has to do with Dale’s precious drum set. Right before Dale finds a chip in one of his drumsticks and launches into a tirade against Brennan, he finds him lying on the couch, drenched in sweat, watching TV. He’s sweaty from playing Dale’s drums, but he’s forbidden from touching them, so he has to make up a lie.

When Dale asks Brennan why he’s sweating so much, he tells him he’s been watching the reality series Cops, which is supposedly so intense that it made him break into a sweat. Even funnier is that Dale’s only onto the lie because he knows that Cops doesn’t start until later.

“Flat. It’s So Flat, I Can’t Even…I Don’t Even Know.”

Derek

The introduction of Adam Scott’s Derek in Step Brothers is hilarious, with Derek also getting a fair few funny Step Brothers quotes. Derek forces his wife and kids to sing Guns ‘n’ Roses’ “Sweet Child o’ Mine” in the car, and while his kids are into it, his wife looks like she’d rather be anywhere else. And it doesn’t help that when she’s singing, Derek is constantly criticizing her pitch.

Derek’s true character as an absolute jerk is revealed upon his introduction. It’s made even more apparent when he bores into his wife for her off-key singing in the car, saying, “This is $1200 a week for voice lessons, and this is what I get?” He attempts to “save” the song by performing his own solo. It’s no wonder his wife Alice makes a pass at Dale.

“Listen, Gang, Don’t Be Mad At Dale For Ruining The Story…And Possibly The Evening.”

Derek

Brennan doesn’t even stay in the house when Derek comes over for dinner when one of the best Step Brothers quotes is uttered. Dale does, but he learns soon enough what a jerk Brennan’s biological brother is. While Derek is recounting the story of why he had to miss Robert and Nancy’s wedding — because he was bonito fishing with Mark Cuban and other famous people — Dale interrupts and asks if bonito are big fish.

Robert gets angry at Dale’s interruption, but Derek addresses the issue by saying sarcastically not to be mad at Dale for ruining his story, or the entire evening, for that matter. All of this tension between Derek and Dale leads to Derek getting punched in the face later inside the tree house.

“I’m Dale, But You Have To Call Me Dragon.”

Dale

You can tell these guys like ‘80s cop shows and Jean-Claude Van Damme movies from the offset based on their chosen monikers, leading to one of the best Step Brothers quotes. They demand to be called these nicknames — Dragon and Nighthawk — which they’re pretty much never called again, right before the title of the movie appears between them on-screen.

This is also an important moment in the movie, because it’s the first meeting of the central duo. At first, they hate each other, but they’ll eventually grow to love each other. That’s sort of foreshadowed here by how much they have in common.

“I Would Follow You Into The Mists Of Avalon, If That’s What You Mean.”

Dale

At the beginning of Step Brothers, Dale and Brennan hate each other. But then they find a common enemy in Derek, Brennan’s brother, who wants to sell their parents’ house and kick them out. As soon as John C. Reilly’s Dale punches Derek in the face, they’re the best of friends, which brings about one of the most hilarious Step Brothers quotes.

When declaring their friendship for one another, Brennan goes into a long-winded speech about how at first he hated Dale, but after the “courageous act that you showed me against the one they call Derek,” Brennan hopes that he and Dale can be the kind of friends who “ride majestic, translucent steeds.” Dale answers his newfound friend with the ridiculous line above.

“Robert Better Not Get In My Face…‘Cause I’ll Drop That Motherf**ker!”

Brennan

It’s not easy to have to get to know a new stepparent, and some of the best Step Brothers quotes come from Dale or Brennan (poorly) coping with the new additions to the family. It would be great if everyone could get along, and it could be a seamless transition from the old situation into the new situation, but it’s tough.

Of course, it should be a little easier than Brennan makes it, since he’s 40 years old, but his childish response to the situation is what makes these quotes from Step Brothers work so well. He expects a series of fights to happen between him and Robert to determine who’s the alpha male.

“Boats ‘N’ Hoes, Boats ‘N’ Hoes”

Dale And Brennan

When Brennan and Dale fail to get hired at any of their joint job interviews in the Certified Rotten comedy film, they decide to give up on their pursuit of employment and go out on their own to start a multinational entertainment company called Prestige Worldwide. Their first clients are Huff ‘n’ Doback, their own hip hop duo, whose debut track is “Boats ‘n’ Hoes,” prompting one of the most iconic of all the Step Brothers quotes.

They shot the music video on Robert’s boat (“Nachos and lemonheads on my dad’s boat / You won’t go down, ‘cause my d**k can float!”) and ended up crashing it into some rocks. They premiere this absurd video at Derek’s birthday dinner, hoping he’ll invest in this new business opportunity and none of it went to plan

“Stop Being A F**king Dinosaur And Get A Job.”

Robert

Actor Richard Jenkins doesn’t get many funny Step Brothers quotes. Rather, the humor of Robert’s character comes from his reactions to Dale and Brennan’s antics. But he does get one monologue at the Catalina Wine Mixer in which he’s trying to identify with his two sons, while at the same time imploring them to finally grow up, but never forget what keeps one young.

Robert goes into a tale about how when he was a kid, all he wanted was to be a Tyrannosaurus Rex, so much so that he would make his arms short, roar, and chase neighborhood cats. He explains that when he was 17, his father told him it was time to “throw childish things aside” but in actuality, he said one of the funniest Step Brothers quotes listed above.

“This House Is A F**king Prison!”

Brennan

Will Ferrell and John C. Reilly play Brennan and Dale as the most ungrateful pair of children who ever lived. They’re 40 years old and still get handed everything by their parents, and yet they’re still not happy. Dale and Brennan have some of the best Step Brothers quotes, but the one where Brennan says the house is a prison, and Dale interjects “on Planet bullsh*t” is one of the most hilarious.

They claim to be prisoners, just because they were grounded and lost their TV privileges for a week after destroying half the house in a “savage fight” that attracted the entire neighborhood’s attention. What’s great about this line is that it takes things a few steps further, possibly with improvisation from the actors.

“I’ve Been Called The Songbird Of My Generation.”

Brennan

Brennan definitely thinks highly of himself, and this entry to the Step Brothers quotes list proves it. Will Ferrell sings in a lot of his movies. In The Other Guys, he sings that depressing song about children getting pinkeye and having their Harry Potter books burned with those guys at the bar. In Elf, he sang a duet with Zooey Deschanel while she was in the shower.

In Step Brothers, he sings “Por Ti Volaré” like a genuine opera singer, with backing drums performed by John C. Reilly. According to Dale, his voice sounds like a combination of Fergie and Jesus, which is right in line with his absurd character and is so over the top that it’s funny.

“You’re Embarrassing Yourself, You Geriatric F**k!”

Brennan

In the rewatchable Will Ferrell film, Brennan and Dale expect to premiere their “Boats ‘n’ Hoes” video to glowing reviews from everyone at Derek’s birthday dinner, followed by everyone getting out their checkbooks to invest. When that doesn’t happen, Brennan gets a little testy towards Robert and shouts out one of the funniest Step Brothers quotes.

Brennan in particular is no stranger to bizarre threats. At Derek’s birthday, he demands that Robert write them a check for $10,000, or else he’s going to “shove one of those fake hearing devices so far up your a**, you can hear the sound of your small intestine as it produces s**t!” He also mentions that Robert should keep his hands off of his mother, for good measure.

“Dad, What Are You Doing? It’s Shark Week!”

Dale

Step Brothers was conceived after director Adam McKay saw the hilarious chemistry between Will Ferrell and John C. Reilly in his previous movie, Talladega Nights: The Ballad of Ricky Bobby. So, he came up with a weird, little, absurdist comedy about a pair of 40-year-old men who still live with their parents, and have to live with each other when their parents get married, eliciting these hysterical Step Brothers quotes.

While Ferrell is predominantly a comedy guy and Reilly is better known as a dramatic actor, the latter holds his own comedically and has just as many memorable lines and scenes as Ferrell. In this scene, Brennan and Dale are watching Shark Week on television, when Robert and Nancy walk in to speak with them, and Robert turns off the TV. This prompts Dale to say the above line indignantly.

“You And Your Mom Are Hillbillies. This Is A House Of Learned Doctors.”

Dale

The whole bedroom scene in the Adam McKay movie on Brennan’s first night in the new house is full of the best Step Brothers quotes. As it devolves, they start talking about what they’re going to do when the other one falls asleep (“I’m gonna fill a pillowcase full of bars of soap and beat the s**t out of you!”). But it’s Dale’s delusional declaration that he’s a “learned doctor” and Brennan is a “hillbilly” that takes the prize for the most memorable quote in the scene.

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