The Biggest Breakthrough Comedy Performances of the 21st Century

All acting careers are difficult things to navigate. Hell, most acting careers don’t even exist.

If you are lucky enough to make a career in the entertainment industry, you have to make shrewd decisions on what your next project will be, as it could very well be your last.

No subset of actors are more aware of this than comedic stars.

3-5 years, if you’re very, very, very lucky, is about how long the world cares about your particular brand of funny, before they’re on to the next big thing.

It’s not the audience’s fault, necessarily.

Comedy is about surprise.

It’s hard to surprise people with your take on comedy after people have seen it in several big movies, or TV shows, over several years.

On the flip side, these breakthrough performances are so memorable because of just how unexpected they were.

With a short shelf-life in mind, it’s wonderful that we have any of these people in our lives, for as long as the box office will allow.

There were only two factors I considered in this list:

  • perceived cultural impact (how well is this person known? how talked about was their breakthrough performance?), and
  • how much of a breakthrough was their “breakthrough performance” (in comparison to their personal ubiquity before “the breakthrough”)?

Will Ferrell might be the biggest comedic star of the 21st century, but did he really “breakthrough” in the 21st century?

Let’s take a look.

#7. Will Ferrell, Old School

Will Ferrell would have been a lot higher on this list had his “breakthrough” been a little more breakthrough-ish.

Being the funniest person on Saturday Night Live isn’t exactly a role in need of exposure.

Best Will Ferrell Patriotism GIFs | Gfycat

And co-starring in a major motion picture, 1998’s A Night at The Roxbury, may be equally conspicuous.

But it was perhaps because he starred in A Night at The Roxbury that his role in Old School felt like such a revelation, because it wasn’t clear after Roxbury that Ferrell would make the transition to the big screen successfully.

And success in the 21st century, in Will Ferrell’s case, is being as Will Ferrel as he can be – as we had known him on SNL – on film.

2003’s Old School set Will Ferrell on the path to become Will Ferrell as we now know him.

But due to the fact he had a lot of success before Old School and that success was in the 20th century, he’s kind of on the borderline for this category, hence his late entry into this list.

#6. Karan Soni, Deadpool 2

As soon as Deadpool 2 hit theaters in the summer of 2018, it seemed liked Soni was everywhere.

And for someone who didn’t see Deadpool 2 in theaters, this was a bit confusing.

He guest-starred on the criminally underrated shipwreck comedy, Wrecked and the just-regularly underrated cop comedy Brooklyn Nine-Nine, going on to play supporting roles in Pokemon Detective Pikachu and Always Be My Maybe.

While he was co-lead, alongside Harry Potter and Steve Buscemi, on the Simon Rich TBS series Miracle Workers, he, perhaps most ubiquitously, and foreshadowing the May release of Deadpool 2 starred in this nationwide Diet Coke commercial in February 2018.

Commercials wouldn’t have been considered a career next step through most of Hollywood history, but there were a lot of 20th century Hollywood traditions that were not worth propagating.

#5. Awkwafina, Crazy, Rich Asians

While Ocean’s 8 was technically released earlier in the summer of 2018, it’s pretty safe to say it didn’t have the cultural impact of Crazy, Rich Asians, unless you measure impact strictly in things neckbeards are upset about.

Since her Crazy, Rich Asians breakthrough…

Her Pixel 3a commercials with 2 Chainz were up there alongside Lil Wayne’s champagne pouring Samsung S7 commercials in the category of Funniest Phone Commercials Featuring a Rapper.

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Awkwafina has her own, funny sitcom (Nora From Queens) on Comedy Central that just ended a successful first season.

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And she’s shown up in Jumanji: The Next Level, The Angry Birds Movie 2, and Between Two Ferns: The Movie.

Not bad for a 21st century comic breakthrough.

#4. Tiffany Haddish, Girls Trip

Tiffany had 12 years worth of imdb-worthy roles before Girls Trip but none of them catapulted her to best-of-the-season SNL hosting gigs, lead roles in major studio movies, or asking kids what kind of businesses they have on Kids Say the Darndest Things?

She is now a household name, on a level no other black woman has reached – through comedy – since Whoopi Goldberg?

Wow, didn’t think about that until I wrote it but it might be true.

#3. Jack Black, High Fidelity

Jack Black steals every scene he’s in in 2000’s High Fidelity.

And he does it in the complete, untamed, Jack Black fashion that the world has now come to take for granted.

Jack Black School Rock GIF - JackBlack SchoolRock LikeTheDelivery ...

If we are to avoid recency bias, Jack Black’s breakthrough in the early 00s was as big as any comedy star (or 3rd biggest) in the 21st century.

If you haven’t seen the recent Jumanji remake, it’s 100% worth your time (the first one, and the second half of the second one, when the writers realize – too late – the mistake they had been making all movie) and it is a great reminder of the hilarious, spontaneous energy that Jack Black can bring to any movie.

#2. Zach Galifianakis, The Hangover

Of all on this list, no one went from lesser known to more well-known than Zach Galifianakis playing Alan Garner in The Hangover.

Sure, Galifianakis had a 1 season, 36 episode, ambitious late night talk show called Late World with Zach, but you wouldn’t recognize him from it.

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While fans of stand-up became aware of Zach from his 2006 special Live From the Purple Onion and the 2005 Comedians of Comedy – which gave the comedian a Hedbergian cult-like status – it wasn’t until the biggest comedy of the 21st century that his talent was recognized on a worldwide stage.

#1. Melissa McCarthy, Bridesmaids

I had no idea who Melissa McCarthy was before Bridesmaids even though she co-starred on CBS Mike & Molly since 2010.

Like most on this list, Melissa had roles in other relative-to-normal-people “high profile gigs”.

But a breakthrough to household notoriety does not a CBS sitcom make.

Since Bridesmaids she’s had 3 $100 Million box office movies (“Spy,” “The Heat,” and “Identity Thief”) and while this list is not based on box office, but rather, that less tangible “cultural impact” + “degree to which their breakthrough project was a true breakthrough”, it’s worth noting that none of these were sequels to her breakthrough film (no tea, no shade Zach Galifianakis).

Bridesmaids (2011) Quote (About restroom plane scene gifs flight) - CQ