Though the misadventures of Sunny, Klaus, and Violet Baudelaire are the heart and soul of A Series of Unfortunate Events, the laughs come from the profoundly transparent and intentionally ridiculous disguises worn by Neil Patrick Harris as Count Olaf.
Cynthia Summers, the costume designer for Seasons 2 and 3 of A Series of Unfortunate Events, has referred to her approach in creating the costumes as "period fantasy," which cribs from '60s, '70s, and '80s fashion. This means that part of the charm of Olaf's bad disguises is their retro vibe. A good Olaf disguise is mostly connected to how ineffective it is at disguising Olaf, but a great Olaf disguise is not just a bad disguise, it combines actual high fashion for hilarious hyperbole.
So which Neil Patrick Harris Count Olaf disguise is the best? Let's use humor and fashion as our dual criteria and rank all 13 nefarious costumes one by one.
Coach Genghis from The Austere Academy
We’re ranking this one last only because the name “Genghis” refers to Genghis Khan, and Count Olaf rocks a turban to pull it off. Sure, Olaf’s disguises are supposed to be dumb and obvious, but because this get-up borders on cultural appropriation, its effectiveness is just not that funny.
Stefano from The Reptile Room
Though this is technically Count Olaf’s very first disguise in the series, the bald scary Stefano is good but just not as memorable as the other over-the-top disguises from later in the series.
Matthias Medicalschool from The Hostile Hospital
In the book version of The Hostile Hospital, Count Olaf mostly appears via an intercom rather than in person. But in the show he’s dressed as a horrific surgeon. It’s scary, and NPH pulls it off like he’s doing a spoof-horror movie, but it’s not even close to being the best.
Al Funcoot from The Bad Beginning
Al Funcoot is a fake playwright who serves as Olaf’s nom de plume in the first book. Not his funniest disguise (maybe not even a disguise?) mostly because it’s just on paper, but the references Olaf makes to this name in the new season are hilarious.
Ringleader from The Carnivorous Carnival
NPH’s carnival ringleader outfit in The Carnivorous Carnival is a cross between a David Lynch movie, something out of Tim Burton’s closet, and an unfilmed Michael Jackson video. In other words, awesome, if a little bit derivative in its “weirdness.”
Captain Sham from The Wide Window
Now we’re talking! NPH becomes a sea captain, complete with his own business card to prove it. Chronically, The Wide Window is only the third book, meaning this really kicks off the hilarious and absurd costumes. Later in the series, we learn that the sea captain disguise is one a ton of other VFD agents rock, too.
Shirley from The Miserable Mill
Count Olaf’s Shirley in The Miserable Mill is perhaps the apex of the first season of A Series of Unfortunate Events. It feels like NPH is having the most fun in this disguise, and the fake relationship between “Shirley” and Dr. Orwell is pretty much the best part of that particular installment.
Yessica Haircut from The Bad Beginning and The Ersatz Elevator
Unique to the Netflix series, this is a half-assed disguise Olaf uses to infiltrate Mr. Poe’s office on more than one occasion. This one is funny mostly because of the alias, “Yessica Haircut,” which Olaf seems to invent on the spot.
Jacques Snicket from The Penultimate Peril
In the Netflix version of The Penultimate Peril, Olaf briefly impersonates Lemony’s brother, Jacques Snicket. This involves him calling attention to the fact that he is “definitely not dead” and insisting the tuxedo is stolen, not rented ... even though later he clearly admits it's rented because he’s worried about the tux being dry-clean only! Pretending a tux is stolen and not rented when it's really rented is maybe the funniest joke in the whole series.
American tourist dad from The Grim Grotto and The Penultimate Peril
Also unique to the series, the “average” American dad disguise Olaf uses when trying to rent a submarine is hilarious mostly because of the affected voice he uses. Where is that even coming from? NPH sounds like a bad British actor doing an American accent in a made-for-TV movie. It’s also great because the disguise is irrelevant; there’s a submarine already rented for them under Esme’s name.
Kit Snicket from The End
Olaf’s final disguise in the series finds him throwing some seaweed in his hair, sticking a diving helmet under his shirt, and talking in a high voice. This is his attempt to act like a pregnant woman named Kit Snicket, who is, in fact, lying about 50 feet away from him in the same scene. Not only is this visually absurd, but the real joke is that of all of Olaf’s disguises, this is the only one which fools no one.
Detective Dupin from The Vile Village
It’s a close tie for the top two slots for the best Count Olaf Neil Patrick Harris disguises, but these last two are far and away much funnier than any of the other disguises put together. (Interestingly, these disguises occur in back-to-back books, too.)
Referencing Edgar Allan Poe’s famous fictional detective, Olaf uses the name Detective Dupin but acts like a bad beat poet/cop from an undefined bygone era. In the book, he snaps his fingers and insists things are or are not “cool.” But, in the show, he does a bizarre scat-rap thing to describe how he’s solving “mysteries.”
Honestly, I could watch the scene where he raps about Jacques Snicket over and over again. Judy Punch’s weird Russian cop persona is equally hilarious in this episode, too, proving that Olaf really is at his funniest when he’s teamed up with Esme.
Gunther from The Ersatz Elevator
In the book version of The Ersatz Elevator, “Gunther” is a fashionable, bizarre European advisor to Esme Squalor. Since his look wasn't actually that well-defined in those pages, costume designer Cynthia Summers had a lot to play with for the Netflix show. And so, in the show, Olaf goes full-on Karl Lagerfeld, complete with totally unnecessary leather fingerless gloves. The dance sequences between Neil Patrick Harris and Judy Punch in this episode is worth the entire series.