Top 10 Times Deadpool Roasted Pop Culture

Top-10-Times-Deadpool-Roasted-Pop-Culture

Welcome to WatchMojo, and today we’re counting down our picks for the times that the Merc with a Mouth skewered figures and moments from outside the Marvel Universe.

#10: Deadpool Roasts Trailers

“Deadpool 2” (2018)
In case you needed further proof that Wade Wilson can’t take anything seriously, just look to this characteristically irreverent trailer promoting the franchise’s first sequel. Initially, the trailer appears to be advertising a dark, gritty, dramatic Cable film — which, hey, we definitely wouldn’t turn down. Nearly 30 seconds pass before Reynolds’ most iconic character literally stops the proceedings by pausing the trailer and lambasting an unseen “Dale,” before referencing the famously troubled production of Warner Bros.’ “Justice League.” The rest of the trailer sees Deadpool taking matters into his own hands… by childishly using action figures to act out the plot’s broad strokes.

#9: Deadpool Roasts Liam Neeson

“Deadpool” (2016)
Okay, so Deadpool isn’t exactly the best judge of character. No one is disputing this. That said, he does raise a pretty good point as to the existence and primary plot of the “Taken” franchise. While in bed with Vanessa, Wade awakens in a cold sweat, revealing that he’s had another “Taken” nightmare. For the uninitiated, these highly meme-worthy movies starred Oscar nominee Liam Neeson as a retired CIA officer whose family is repeatedly kidnapped — the films follow Neeson’s efforts to retrieve them. Wade remarks that, after three movies, one has to wonder if Neeson’s character is any good as a father. Possible setup for a “Deadpool” + “Taken” crossover? Almost certainly not. But wouldn’t that be something?

#8: Deadpool Roasts T-Shirts

“Deadpool” (2016) & “Deadpool 2” (2018)
Admittedly, this entry isn’t a “roast” as much as it is a “loving homage.” In the first “Deadpool” film, your friendly neighborhood ‘Pool guy is seen prominently sporting a t-shirt bearing “Golden Girls” star Bea Arthur’s likeness. Ryan Reynolds reportedly met with the late performer’s estate and paid $10,000 out of his own pocket for the rights to Arthur’s face (that money was donated to charity). Always one to outdo himself, the film’s sequel has Wade wearing an “Olivia & Meredith” shirt. If you’re a Swiftie, you might recognize the pair as pop star Taylor Swift’s beloved kitties. Who knew Deadpool was so in touch with his feminine side?

#7: Deadpool Roasts Musicals

“Deadpool 2” (2018)
It probably goes without saying that the “Deadpool” franchise is hardly family-friendly viewing. That said, as we’ve explored on our channel before, Deadpool is no stranger to letting the Walt Disney Company have it. In a hilarious bit of meta-comedy, a clip from Barbra Streisand’s 1983 classic “Yentl” plays in “Deadpool 2,” featuring Babs singing “Papa, Can You Hear Me?” After Vanessa meets her (short-lived) untimely end, Wade is heard singing “Do You Wanna Build a Snowman,” famously of the “Frozen” soundtrack. The deadly assassin then muses that the two songs bear more than a passing resemblance.

#6: Deadpool Roasts Ryan Reynolds’ Family

“Deadpool & Wolverine” (2024)
Did you need further proof that Deadpool has precisely 0 filter? Oh, you didn’t? It kinda went without saying? Either way, let us break it down for you. Series star and co-writer Ryan Reynolds has never shied away from roasting himself, and in “Deadpool & Wolverine,” the Canadian-born actor’s family takes some of that heat. Early on, Deadpool quips that “Gossip Girl” — the CW teen drama that gave Reynolds’ wife Blake Lively her start — puts him… ah… in the mood, let’s say. Lively later shows up in the film as Lady Deadpool, a Deadpool variant, while the couple’s children each having their own cameos.

#5: Deadpool Roasts, Like, Every Pop Singer

“Deadpool 2” (2018)
Once again, we think these roasts were executed (no pun intended) with genuine love and fandom. In “Deadpool 2,” the titular character name-drops several pop stars, both living and, you know, not living. The opening credits sequence is set to Dolly Parton’s “9 to 5,” with Reynolds referring to her by name. Deadpool also quips that he wants to name his and Vanessa’s potential child “Cher,” which he later reiterates over her “If I Could Turn Back Time.” George Michael and David Bowie are referenced, with ‘Pool mourning the former while quoting “Careless Whisper” and taking solace in the fact that Bowie is still around. Uh… who’s gonna tell him?

#4: Deadpool Roasts Josh Brolin

“Deadpool 2” (2018)
We wonder if Brolin knew the degree to which Reynolds-slash-Deadpool would be taking aim at his long and storied career. Or maybe he contributed the roasts himself? In any case, the Oscar nominee is clearly a good sport. The most obvious target in Brolin’s career is that, while he plays the mutant Cable in “Deadpool 2,” he’s better-known for his iconic role as MCU baddie Thanos — which Deadpool explicitly references. The Merc also roasts the actor himself: attempting to physically describe Cable, Deadpool notes that Brolin isn’t quite comics-accurate casting. Careful, ‘Pool: we’ve heard this guy’s inevitable.

#3: Deadpool Roasts Warner Bros.

“Deadpool & Wolverine” (2024)
Was this all-too-brief “Deadpool & Wolverine” cameo the movie’s most epic? While the jury’s still out on that one, audiences can’t deny the charge they felt when a Wolvie variant turned around to reveal Henry Cavill’s blindingly-handsome mug. In short: Cavill played Superman in the ill-fated DC Extended Universe, receiving critical and fan acclaim for his performance. Unceremoniously ousted from the role following the critical and commercial failures of several DCEU films, the “Cavillrine” acknowledges that the actor is a popular choice for fan-casting the mutant, not to mention his tenuous relationship with the studio that distributed the films of DCEU.

#2: Deadpool Roasts Ferris Bueller (& The Audience)

“Deadpool” (2016)
By the time the first “Deadpool” film rolled out into theaters in 2016, superhero movie fans were well-acquainted with the infamous post-credit stinger, which had, at that point, appeared in nearly every MCU movie until that point. As such, fans knew that, given Deadpool’s reputation for making fun of superheroes, this trend would be roasted in some way. In the character’s typically meta fashion, the “Deadpool” post-credits scene features Reynolds reenacting the stinger from “Ferris Bueller’s Day Off,” in which Matthew Broderick admonishes the audience for having stayed in their seats. Deadpool puts a twist on this by lazily proposing elements that could appear in the film’s sequel, seemingly roasting the MCU’s tendency to include heavy foreshadowing in their post-credits scenes.

#1: Deadpool Roasts NSYNC

“Deadpool & Wolverine” (2024)
For one brief, shining moment, “Deadpool & Wolverine” had us reliving the glory days of the early 2000s, when gas was cheap and boy bands ruled the world. As the Merc handily dispatches a group of Time Variance Authority soldiers intended to bring him to Mr. Paradox, the shocking violence is interspersed with the titular character reenacting the iconic choreography from the “Bye Bye Bye” music video. Unfortunately, the moves aren’t all Reynolds’ — while the actor handles some of the simpler moves, they’re mostly performed by Nick Pauley, a dance double. At least he’s credited as “Dancepool.”

What was your favorite “Deadpool & Wolverine” moment? Let us know in the comments!