Roll call for J’Quellins, B’Lakes, D-Nices, A-A-Rons, and anyone else who doesn’t want to get sent to Oshack Hennessy’s office by inner-city substitute teacher Mr. Garvey!
As the creator and star of one of the most popular and widely quoted comedy sketch shows of all time, Keegan-Michael Key is a brilliant actor, writer, and producer known for his outlandish characters.
However, his comedic chops run the gamut as he has had numerous supporting roles in genres from family to raunchy. Beyond television, he has graced his fair share of movies, and his presence, no matter how brief, always stands out as the scene-stealer that he is.
Having been in the entertainment industry for almost twenty-five years, Key has amassed twenty-three award nominations, including three wins with a Peabody, an American Comedy Award, and an Emmy for Outstanding Variety Sketch Series.
We combed through the comedian’s career to compile a list of some of the greatest works of the multifaceted Keegan-Michael Key. Much like the actor’s choices in creative endeavors, there is a little something for everyone.
While some of the works listed below include his most well-known projects, we’ve brought a few forgotten classics and hidden gems to light.
Caution: Ribs may be cracked, and funny bones may be tickled.
Teacher of the Year (2014)
Role: Ronald Douche. Available to watch on Peacock.
The story is portrayed in a mockumentary format centering around a high school educator who is nationally recognized with the “Teacher of the Year” award, prompting the ire and jealousy of his fellow faculty members.
Among those members is Ronald Douche, played by Key. Unlike some of the other school staff, Douche is intent on trying to share the spotlight in the most desperately hilarious of ways that are combined with a perfect balance of dry humor and over-the-top reactions.
Keegan-Michael’s performance was the movie’s breakout and is still praised as the film’s highlight for his comedic timing. This movie is excellent for anyone who enjoys the mockumentary style, such as Best in Show and Abbott Elementary.
Keanu (2016)
Role: Clarence Goobril. Free to watch on Tubi.
This buddy action comedy was the first film endeavor of the starring duo after their wildly successful sketch comedy series. The story’s premise is simple enough as it centers around two cousins who infiltrate a gang to retrieve their stolen kitten.
However, this movie shines in how both actors supercharge their characters with comedy. Key’s portrayal of Clarence from an uptight team-building coach to a hardened thug delivers gut-busting laughs throughout.
Key and Peele draw on their chemistry to fully embody the buddy aspect of this movie with a comedic dynamic much like other action duos in 21 Jump Street and Lethal Weapon.
Win It All (2017)
Role: Gene. Available to watch on Netflix.
While this gambling comedy doesn’t have Key in the lead role, his presence is very much felt through interactions with the main character. The plot itself involves an avid gambler who agrees to hold on to the bag of a prison-bound friend before discovering the duffel is full of cash. Cue the mayhem.
Playing a Gamblers Anonymous sponsor to Jake Johnson’s Eddie Garrett, Key pulls out a drier approach to this comedy, delivering more subtle humor compared to his more outlandish roles.
This is a great film for anyone who enjoys stories of addiction in a more comedic vehicle like the series Shameless or a softer approach like Mom.
Dolemite Is My Name (2019)
Role: Jerry Jones. Available to watch on Netflix.
This biographical comedy focuses on the real-life Rudy Ray Moore, played by Eddie Murphy. It portrays the titular character during the era in his life when he developed his phenomenal namesake in the 70s.
Key plays Jerry Jones in another supporting role. Apart from a few details, Jones and Key share many parallels — both are actors and screenwriters — though Jones was more dramatically inclined. Still, Keegan-Michael Brings his perfect timing that fits right into a dynamite Eddie Murphy film.
This is an excellent movie for anyone who enjoys stories about overcoming obstacles in the entertainment industry, such as The Disaster Artist or shows like The Offer.
Wendell & Wild (2022)
Role: Wendell. Available to watch on Netflix.
Pairing the comedic duo of Key and Peele together again, Wendell and Wild brings Angela Bassett along for this Burton-esque stop-motion-animated horror comedy that revolves around two scheming demon brothers who wrangle a young girl into helping them get to the land of the living.
Voicing the character of Wendell, Key infuses the stop-motion character with a larger-than-life portrayal, utilizing all the gravitas and experience of a well-seasoned actor through timely inflections and perfect comedic pitch.
This movie is like a combination of Beetlejuice and Coraline, another of the director Henry Selick’s films. It is a perfect choice for anyone who enjoys a dark sense of humor involving scrutinizing children and suspicious adults, much like Lemony Snicket’s A Series of Unfortunate Events.
Mad TV (2004-2009)
Role: Various. Free to watch on Sling TV.
While plenty of sketch shows have come and gone, few could hold on as long and firmly as Mad TV. Loosely inspired by the humor magazine Mad, this show was meant to contend with the juggernaut that is SNL.
Key joined the cast in the series’ ninth season and continued on until its fourteenth and final in 2009. His most notable character is Coach Sandoval Hines, the stereotypical quick-tempered high school coach who wore shorts far too short and threatened his students far too often.
While the show has been off the air for a decade and a half now, many Mad TV sketches continue to hold their humor as the show has managed to stand the test of time. This is a great watch for anyone who is an avid viewer of Saturday Night Live.
Key & Peele (2012-2015)
Role: Himself/Various. Available to watch on Hulu.
The show most responsible for Key’s noteriety is the one he shares his name with. Created with fellow comedian Jordan Peele, Key & Peele produced some of the most memorable and comedic sketches about American pop culture, ethnic stereotypes, social awkwardness, and race relations.
The series earned many nominations as well as three wins, including two Emmys. The show lives on through an official YouTube channel run by Comedy Central that has amassed over a billion views.
While it falls under the category of a sketch show, Key & Peele set its own standards to the point that it is in a league of its own.
SuperMansion (2015-2019)
Role: American Ranger/Sgt. Agony/Blue Menace. Available for purchase.
SuperMansion was an animated stop-motion sitcom about a team of superheroes that strongly parodied the Justice League and similar hero groups. The show ran for three seasons from 2015 to 2019.
Though the series was short-lived and not very loved by critics, the voice cast was star-studded, including Bryan Cranston, Heidi Gardner, Jillian Bell, Yvette Nicole Brown, and Chris Pine. Among that list is also Key, who voiced three roles in the show, as is typical for comedic actors of his caliber.
Add this to your list if you enjoy adult animation like Family Guy and South Park or specifically stop-motion animation comedy like Robot Chicken.
Schmigadoon! (2021-2023)
Role: Josh Skinner. Available to watch on Apple TV+.
Yet another star-studded show, Schmigadoon! is about a couple, played by Keegan-Michael Key and Cecily Strong, who are on the rocks and have their lives turned upside down when they are transported to a musical town.
Josh Skinner, a staunch hater of musicals, is no match for the charming residents of this new reality. Gracing the screen are some of the most familiar faces in TV, including Fred Armisen, Dove Cameron, Kristen Chenoweth, Alan Cumming, Jane Krakowsi, Tituss Burgess, and Martin Short.
Sure, this is a great choice for musical lovers everywhere, but anyone with an appreciation for over-the-top acting that sticks the landing will enjoy its campy and satirical feel.
Reboot (2022)
Role: Reed Sterling. Available to watch on Hulu.
Though loved by audiences and critics alike, Reboot only aired for one season of 8 Episodes. The series followed the cast of an early 2000s sitcom in the midst of having their show rebooted by a young writer with a love for the original who is trying to take it in a fresh and more progressive direction.
Key plays Reed Sterling, a Yale-educated actor who portrayed the stepdad on the former show “Step Right Up” but left to pursue more serious roles — only to have his career crash and burn. Keegan-Michael plays the character as if depicting his own possible life path had he not paved his way through comedy.
If down-trodden characters toeing the line between ambitious positivity and soul-crushing reality in a sharply comedic execution like Hacks or Curb Your Enthusiasm is your cup of tea, then give this short-lived hidden gem a watch.
Elsbeth (2024)
Role: Ashton Hayes. Available to watch on Paramount+.
A spinoff of a spinoff, Elsbeth follows the offbeat and sometimes off-putting character of Elsbeth Tascioni, a former successful defense attorney now working alongside the NYPD to investigate murder cases.
Ashton Hayes is a wealthy financial advisor who finds himself under the titular character’s narrow scope after his daughter’s new husband is found dead during the wedding reception at the family’s country club. Death definitely did them part.
Elsbeth features familiar faces as episodic killers dispatching their victims in obscure and, at times, campy ways. While police procedurals focusing solely on murder can be grim, this show delivers positivity through its main character and guest appearances like Key.
Keegan-Michael Key has solidified himself as a powerhouse of talent in the acting and writing community. He will likely continue creating and developing projects that amuse audiences for another twenty years and beyond.
Which among these are at the top of your watch list? Did we miss any of your favorite titles? Drop a comment below and let us know!
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Joshua Pleming is a staff writer for TV Fanatic. You can follow him on X.
