20 Funny Roasts for Chicago Cubs Fans

Funny Roasts for Chicago Cubs Fans

Looking for the best punchline you can use to give a “Cubs fan” sh*t for their poor choice of a baseball team? Look no further. 

In this article, I’ve gathered 20 of the best roast lines that are sure to get a Chicago Cubs fan pissed off, especially if you want to do it hilariously. 

Table of Contents

List Of 20 Funny Roasts to Tell Chicago Cubs Fans

1. What is the difference between the Chicago Cubs and a mosquito? A mosquito stops sucking.

Cubs fans are known for waiting a long time before finally winning the World Series in 2016. 

So you can use this as a way of teasing the Cubs for not winning much for a really, really long time.

The mosquito part adds a touch of humor, implying that the irritation from the Cubs (not winning) goes on and on, unlike a mosquito that eventually stops bothering you.

  • Why are the Chicago Cubs like a sleepy mosquito? Well, at least the mosquito stops buzzing after a while, but the Cubs just keep ‘sucking’ for years!”
  • “Ever notice the Chicago Cubs and a mosquito? A mosquito quits buzzing, but the Cubs? They’re pros at not quitting the ‘sucking’ game if you catch my drift!”

2. “The Cubs have more rebuilding seasons than a construction company.”

Remind them the Cubs are stuck in a constant state of trying to get better but never quite reaching the top.

The comparison to a construction company suggests they’re always a work in progress, never finished – and definitely not winning any championships. 

It’s not just a tease; it’s basically saying the Cubs are more about rebuilding than winning. For a fan, that hurts. 

3. “The only thing the Cubs consistently catch is disappointment.”

Joke about how disappointment seems to be a regular thing for them. It’s a playful dig, making fun of the tough times Cubs fans have been through. 

It’s a bit of a roast, acknowledging the struggle but also making them smile (or maybe cringe a little) about being a Cubs fan.

  • “The Cubs are like professional heartbreak catchers.”

4. “Cubs fans have a better chance of finding Atlantis than a recent World Series win.”

Ridicule the Cubs’ long history of not winning the World Series for 108 years until 2016.

You can use this roast punchline as a clever way of highlighting the team’s historical struggles and playfully poking fun at their championship drought. 

For Cubs fans, it might feel like a funny yet slightly painful reminder of the challenges their team has faced.

  • “Finding Atlantis seems easier than the Cubs snagging another recent World Series win.”
  • “Cubs fans have a better shot at discovering Atlantis than celebrating a recent World Series victory.”

5. “What’s the Cubs’ favorite dance? The ‘Wait for it, Wait for it, Wait for it… Shuffle.'”

Make jest of the team’s history and the anticipation that Cubs fans often feel. The “Wait for it” part is a tease about the Cubs always saying, “Wait ’til next year” because they’ve had many years of waiting for success. 

The “Shuffle” adds a bit of humor to the roast, implying that the Cubs are shuffling through seasons without a significant breakthrough.

  • “Why don’t the Cubs excel in dance? Because their favorite move is the ‘Wait, Wait, Wait… Shuffle’ – always delaying the big performance!”

6. The Cubs are proof that anything is possible as long as you are given unlimited chances and a finite number of outcomes.

Mock the struggles they’ve endured, implying that the Cubs’ success isn’t earned but more like a fluke.

So, if you drop this line around Cubs fans, you’re basically poking fun at their team’s hard-fought triumphs, and they won’t be too thrilled about it. It’s like calling their success a cosmic accident rather than a well-deserved win.

  • “The Cubs’ success is proof that if you roll the dice enough times, you’ll eventually get the outcome you want, even if it takes a century.”

7. “The Chicago Cubs have a great history—especially if you’re a fan of ancient history.”

 Funny Roasts for Chicago Cubs Fans

Touch on all the years they spent without winning and all the jokes and curses that came with it. Consider this line a playful dig that brings up the not-so-fun memories of waiting for victory, and it might get under their skin a bit.

8. “Why do Chicago Cubs fans make terrible detectives? Because they never find anything worth celebrating.”

Use this zinger to tap into the years of disappointment and near-misses that Cubs fans endured. You can use it in a way that touches on their history of heartbreak, making light of the challenges they faced in cheering for a team that once had a legendary championship drought.

  • Why are Cubs fans bad at finding things? Because they rarely discover anything to celebrate.”
  • “Why do Cubs fans make lousy detectives? Because they never find anything to celebrate,” 

9. Seeing grown men cry over a Cubs season is as common as catching a cold in winter – it happens every time!

Hint that Cubs fans only cry when their team falls apart – as if happy tears are a rare species in Cubs nation. 

  • “Cubs fans shedding tears after a season is like clockwork, almost like they’ve perfected the art of crying in baseball.”

10. The only thing that divides Chicago more than baseball is its economic gap

Point out the economic gap in Chicago. Imagine teasing someone about their favorite sports team.

Still, then you go a step further and make fun of the city’s economic inequality, suggesting that their pride in the Cubs is only rivaled by how divided the city is financially. 

It’s a roast that hits where it hurts, making the friendly banter a bit too close for comfort. 

11. “How do you make a Cubs fan smile on a Saturday? Tell them a joke on Wednesday.”

 Funny Roasts for Chicago Cubs Fans

Imply that their team consistently disappoints on the weekends. It’s like saying their optimism is so fragile that it needs a midweek pick-me-up just to survive until Saturday. 


Saturdays are usually game days and a big deal for sports fans, so your joke implies their weekends are typically gloomy unless rescued by a midweek joke. 


It’s a playful roast, but for a die-hard Cubs fan, it could feel like a good-natured roast about their team’s performance.

  • “Why do you need a joke on Wednesday to make you smile on Saturday? Are the Cubs not doing well again?”

12. The Cubs are very much like a Corvette – locked away come October, and when it comes out in the springtime, it gets shit on by birds all year.

This roast has a few layers. First, it’s saying the Cubs are like a high-performance Corvette, setting high expectations. 

But then, it takes a dig at them for not performing well in October, the crucial playoff time. That’s like saying, “You’ve got the cool car, but where’s the championship success?”

Then, the line about birds pooping on them all year is like saying the Cubs can’t catch a break. Instead of having a great season, they’re constantly facing setbacks and disappointments. 

  • “The Cubs are like a fancy car, hiding in October and getting bad luck all year – it’s like they’re wearing a target for bird poop in the spring.”
  • “Comparing the Cubs to a Corvette is like saying they’re flashy but disappoint in October. It’s as if they’re a magnet for bad luck, with birds aiming at them all year round.”

13. If you go to Wrigley, you have a better chance at being murdered than seeing Lester throw to first. 

Tease Lester’s blunder, something Cubs fans chuckle about but still love. Another thing you use this punchline to do is poke fun at Wrigley, which is sacred to Cubs fans. 

It’s like playfully dissing something they hold dear – their team and their ballpark. 

14. You’re not lovable losers anymore

Take away a part of what made being a Cubs fan particular. Cubs fans have a deep connection to that underdog charm, and being told it’s gone can feel like losing a piece of their team’s identity. 

  • You’re not the cute losers anymore; you’re just losers now!”

15. I will never be able to roast the Cubs as well as Dusty Baker burned their promising young pitchers.

Dusty Baker was the manager for the Cubs a while back, and let’s just say Cubs fans aren’t fond of that memory.

Comparing someone’s ability to roast the Cubs to Dusty’s handling of young pitchers is like saying, “I can’t make jokes as bad as Dusty made pitching choices.” It’s not a compliment.

Cubs fans won’t appreciate that because it’s a dig at their team’s history of heartbreaks and poor management decisions.

  • “I can’t roast the Cubs like Dusty Baker roasted their young pitchers – talk about a recipe for disaster!”

16. I can’t hate on the Cubs.

 Funny Roasts for Chicago Cubs Fans

Tease them that their loyalty to the team is so strong that they’re like the philanthropists of baseball, sharing the joy of the World Series with everyone but themselves.

It’s a bit cheeky because, deep down, every Cubs fan dreams of their team finally winning it all.

So, you’re sort of poking fun at that dream and challenging them to break the cycle of being the generous fans who help others get to the big stage. 

  • “Cubs fans are so generous, they practically give away World Series chances to other teams!”

17. Some so many people had died without seeing the Cubs win 

This line is not just a light-hearted jab; it’s a cruel reminder of all those years of disappointment. So, that line is more than just a roast; it’s a brutal emotional gut-punch to any Cubs fan.

18. What do you call a reptile that plays baseball? Snake Arrieta.

Take Jake Arrieta, a former star pitcher for the Cubs, and playfully call him “Snake Arrieta.” The snake part is a jab at his pitching style, sly and agile, like a snake on the mound. 

But here’s the real zinger—associating him with a snake implies he’s gone to another team, one that’s probably a rival of the Cubs. It’s like saying he’s ditched the Cubs for the enemy. 

Cubs fans love Arrieta, so hinting at him wearing a rival team’s jersey hits them right in the feels.

  • “Why did the Cubs fan cringe at ‘Snake Arrieta’? Because it’s like saying their star pitcher slithered off to the enemy team – a real fastball to the heart of loyalty!”

19. I thought about telling a joke to a Chicago Cubs fan, but I figured it might be a swing and a miss, just like their playoff luck!

Poke fun at the Cubs’ history of not doing well in the playoffs. For a fan who’s been passionately supporting them, it’s a bit like bringing up painful memories. 

It’s not just a light-hearted joke; it’s a playful jab at something they care deeply about, making it sting a little. 

So, they might respond with a mix of defending their team and feeling a bit teased – all in good fun, of course!

20. Are there any Cubs fans alive who witnessed both the 1908 and 2016 Cubs win?

Use this question to play on the emotional rollercoaster Cubs fans endured. It’s not just asking about championships; it’s a sly dig at the years of suffering and the contrast between the distant past and the recent glory. 

So, it’s not just a casual question.

  • “Ever met a Cubs fan who high-fived during both the 1908 and 2016 wins? Probably not, unless they’ve got a time machine!”


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