Big Sean is no lyrical slouch. The range of emotion he can evoke— from tenderness to inspiration to amusement— is in large part thanks to his verbal dexterity. To examine his punchlines in isolation reveals a unique sense of humor and intelligence. The Detroit native can inhabit the rappity-rap space as well as the story-heavy one. Sean is fluent in the boastful role, but equally comfortable being sincere, which is why he can craft an album that includes both “I Don’t Fuck With You” and “One Man Can Change the World” and no one questions the appropriateness of either track.

Punchlines are a useful measure of lyrical prowess because they require a particular breed of efficacy. Can you be impactful when you need to be? Can you deliver on build-up? Can you write something memorable that sticks in people’s minds? Being able to storytell and write strong lyrics does not necessarily translate into being able to write punchy lyrics. Big Sean is one of the rare artists who can do both. Some of my favorite songs of his aren’t featured on this list (“Ashley” and “Sunday Morning Jetpack”, for example) because even though they have some of his best lyrics, they aren’t formed around punchlines. Big Sean loves a good sports metaphor and there are definite patterns that emerge when you study his punchlines.

Even if he’s not the originator, Big Sean has received a lot of credit for popularizing the hashtag flow— with good reason. Both “Supa Dupa” and “Supa Dupa Lemonade” are essentially punchline after punchline. They’re exercises in wordplay where narrative takes a backseat and the freedom to be nonsensical allows for a vast range of references. Big Sean can exhibit his knowledge of history, pop culture, and any topic he can think of in this loose format that rewards free associating. 

Punchlines are used to broadcast wit. Given how concise and entertaining they are, punchlines are heavyweights when it comes to the caption game. You can find them in spades on Instagram where influencers use lyrical punchlines to show off their music taste. Let’s take a look at some of Big Sean’s best punchlines and source inspiration for that post you have in your queue.

Jerritt Clark/Getty Images for Rolling Stone

Most of social media is bragging. Pictures of a new house, new car, jewelry, exclusive sneakers—you can count on Big Sean to furnish the perfect in-your-face boast to complement your photo. For the flex post:

Bank account got me feelin’ well, Fargo (Supa Dupa Lemonade)

I’m on the top floor getting brains, higher learning (Supa Dupa Lemonade)

People asking me how it happened, man I tell ’em / I Rolex-ed the situation and just had perfect timing (Say You Will)

Priceless is affordable, order what you can’t afford / Matter fact, order more (High Rise)

Worry ‘bout my niggas they’re good, Marshall (Supa Dupa Lemonade)

Yeah, and I got money bags under my eyes, ho, cause I ain’t sleep / They all Goyard too cause I ain’t cheap (B Boy)

I got 99 problems, getting rich ain’t one (All Me)

I’m bringing home dead prez, my house done feel like it’s haunted I put the city on my back, right along with my garments (10 2 10)

A subcategory of the flex vertical: Food/Travel/Private Jets. Apparently, there is a social contract where you must post from nice restaurants and exotic locales. Big Sean has no shortage of punchlines to go with eating filet mignon in a robe in a hotel suite.

Everything fast ‘cept the food, watch what we eating / If it add a couple years to our life, then we might go vegan (Holy Key)

I’m eating lobster with my shrimp hand (Mona Lisa)

Now we out in Paris, yeah, I’m Perrierin’ / White girls politickin’, that’s that Sarah Palin (Mercy)

All this bread can’t be too good for my cholesterol (10 2 10)

Woodgrain steering wheel, this bitch feel like a pirate ship (No Favors)

Made my blueprints, so my life got no ceilings (Go Legend)

I’m in the Obama suite, you one below up in the Joe Biden (So Much More)

I’m living out my dreams, don’t you dare hit that alarm clock (What U Doin’? [Bullshittin’])

You know when you want to say something to someone’s face, but you’re too much of a coward? Enter the subtweet. It’s IYKYK—but for just one person. Maybe you’re dwelling on your ex or maybe you just want people to think you’re mysterious. Here are Big Sean’s best subtweet worthy punchlines:

Some girls are the Lebron James of playing mind games/And switch their home team up every single time their mind change (Deserve It)

Man, we went from long text, now they shorter than a haiku (Owe Me)

All I want’s a hundred million dollars and a bad bitch/Plus that paper chasin’, it done turn me to a savage (Sanctified)

I guess drama makes for the best content / Everything got a bad side, even a conscience (I Don’t Fuck With You)

Niggas change up more than wishin’ wells / Karma come around I’ll wish ’em well (Bounce Back)

Standin’ next to Jim Carrey, we traded stories, then laughed I said you not the only one I know got rich wearin’ masks (One Man Can Change the World)

Focused on the inner me, never on the enemy (Sacrifices)

Feeling aggressive? Big Sean can weaponize words when he needs to. These punchlines should be used with discretion.

Fuck your two cents if it ain’t goin’ towards the bill (I Don’t Fuck With You)

Hit your girl in my whip and now that pussy got the new car smell (Burn)

So now I’m snappin’ like yo ass just finished the poem (Looking for Trouble)

So futuristic, I’m already over my next bitch (Detroit vs. Everybody)

You gon’ get this rain like it’s May weather (Control)

You forgot where I came from? I’m from where you ain’t from (Don’t Play)

I’m not playing with you, bitch, this not the WNBA (Savage Time)

What’s your favorite punchline from Big Sean? Get the discussion going below.