Great comedy bad guys from movies and TV

While trying to get the most out of our Peacock subscription, I’ve been doing a binge of Parks and Recreation. I’ve been enjoying the Jeremy Jamm character in the later seasons-- douchebag dentist and city council member, where he is the main nemesis to Leslie Knope, a hardworking and caring city servant. He is casually corrupt and exploits the limited power of his office as much as he can. For example, he blocks an initiative to add Flouride to the town’s water, even though all surrounding communities did it years ago, because fixing all the resulting extra cavities paid for his sports car. I didn’t know Jon Glaser, the actor who plays the character, like I do the many other occasional appearances by comedians like Jason Mantzoukas or Ben Schwatrz, who play similar douchey characters. But Glaser’s comedy pedigree is strong, having been a long-time writer and sketch player on Conan O’Brien’s Late Show.

I almost titled this “Great comedy villains”, but I want to keep it open to include great comedic foil characters who don’t quite rise to the level of ‘villain’. Will Arnett’s ‘Gob Bluth’ for example, or Rainn Wilson’s ‘Dwight Schrute’. Of course, an argument can be made that Dwight wasn’t the ‘bad guy’ at all, Jim was the real bad guy of The Office.

For a movie bad guy and definite ‘villain’, I’ll go with the obvious classic Dr. Evil. Mike Myer’s comedy star may have dimmed in recent years, but his sendup of Bond villians, playing a mashup of Ernst Stavro Blofeld and Lorne Michaels, was a terrific character, especially in the first movie, where the concept was more fresh.

(This has been done before it turns out, but almost 20 years ago. Lots of new comedy bad guys have arisen since then…)

I’m watching Season 3 of Picard and my favorite character is Capt. Shaw (Todd Stashwick) as a humorous foil and reality checker to the glurgy ST:TNG cast.

For flat out comedic ‘villain’, you can’t do much better than Prof. Fate (Jack Lemmon) and his sidekick Max (Peter Falk) in The Great Race.

Louie DePalma on Taxi was a great bad guy. If a driver wanted to know about a phone message left for them they would have to give Louie money. He saw characters like Latka and Jim Ignatowski as his personal pawns. The role made Danny DeVito a star.

In a similar vein there was Roy Biggins on Wings. As the owner of successful local New England airline Aeromass he took pleasure in the in the problems facing his small competitor Sandpiper Air. Always ready with an insult and a con he was a delightfully hateful character.

On the TV show MAS*H there was the despicable Frank Burns, a funnier version of the character from the movie, often paired with Head Nurse Margaret Hoolihan who was equally dislikable but morphed into a more human character over time ,largely after the Burns role was written out.

For a true villain there was Siegfried on Get Smart. He was the head bad guy at KAOS, just as bumbling and inept as his good guy counterpart Maxwell Smart.

I…don’t think I ever saw ‘The Great Race’. I’m pretty sure I would remember Peter Falk as a comedic bad guy if I had. I will have to remedy that…

Falk didn’t play many bad guys, but I’m sure he was great at it when he did. I did catch an old “Untouchables” episode awhile back that had a Falk guest appearance as a mob-type guy, and he was great; a charismatic bad guy with a touch of humor.

Oh yeah, classic comedic bad guy. Dany DeVito made a career out of funny bad guys. I remember his lawyer character in the movie ‘Ruthless People’. Basically a much more well-paid Louie DePalma. I still remember his reply to the guy who dialed a wrong number looking for his wife. Not going to print it here though, not even with a spoiler blur!

Larry Linville did a great job playing that character, though I thought it was almost too cartoonish at times. I have to admit though, those MASH episodes were much more fun than the later seasons, when Winchester played a flawed but still decent character, Houlihan as you mentioned became much more humanized, and Hawkeye became a preachy downer. BOOO-ring!

Barry Kripke on “The Big Bang Theory”. Not really a bad guy, more of an antagonist and foil for Sheldon.

Satan, from Highway 61 (1991) - IMDb

Satan may not really be Satan: he may just be a crazy dude. Anyway, he has some screamingly hilarious scenes. In one, he buys the soul of a little girl. In another, he wins at Bingo.

So, so good.

Think Dick Dastardly and Muttley.

Justified also has some incredibly funny villains, including Dickie Bennett–always convinced he’s the smartest guy in the room, always wrong–and Dewey Crowe–so goddamn stupid that you want to feel sorry for him, until you catch along glimpse of his swastika tattoos.

I think they both count as villains, because they 100% cause murder and mayhem. But they’re also such penny-ante crooks, compared to the real nefarious villains of the show, that it’s hard to take them seriously.

One of his earliest roles was a sarcastic mob henchman in A Pocketful of Miracles in 1961. It was Frank Capra’s final film, the production was a mess of clashing egos in a star-studded cast but he called Falk the “one bright spark” in the movie.

Would Q on STNG qualify? John Delancie was tres amusant in that role.

One of Mrs. Solost’s favorite shows. She’s always had a crush on Olyphant. I tried watching it, got though maybe 2/3 of season one and gave up for some reason. I seem to remember enjoying the eps I did see well enough. Sometimes you just get distracted. Maybe I’ll give it another try.

Looks like I have another movie in the Falk oeuvre to catch up on sometime.

Sure! As with the ‘Justified’ example, the show or movie doesn’t have to be a comedy for a bad guy to bring some comedy relief, and Delancie’s Q was very amusing with an undercurrent of menace. A great character.

Heh. The first 2/3 of season 1 is just a crime-a-week show, not much different from Law and Order except with more shootouts. Near the end of season 1, the main story arc picks up.

Season 2 is some of the best TV ever made. Seasons 3-5 are good, and then season 6 just blows me away.

Season 7, released this year and with almost none of the same cast, was an enormous disappointment.

Thanks for the tip!

Sounds like my experience with Breaking Bad-- by the time season 4 was live and it was getting a ton of buzz, I decided to rent season 1 from the library to see what all the fuss was about. Now I think it’s one of the (if not the) greatest TV shows ever made, but I almost didn’t get through season 1. To me the show didn’t hit its stride until seasons 2-3.

One of my all-time favourite TV shows is Jon Glaser’s show Delocated where he plays a clueless guy in the Witness Protection Program (for testifying against the Russian mob) who wants to be a reality TV star. In season 2, there is a guy Sergei who is out to make his life a living hell in some hilariously dark comedy ways.

The movie has nostalgic appeal to me, not the story in the movie, but a rare day when I first saw it as a child. It’s got a lot of good qualities like pairing Bette Davis and Ann-Margret in her first movie as mother and daughter, along with a ton of classic Hollywood supporting players. It contained the first use of the term Godfather for a mob boss in a movie and it’s also a remake of an earlier Capra movie Lady for a Day from 1933. Not a great movie overall but full of wonderful acting bits from the old pros plus the breakout performances from Falk and Ann-Margret.

Brookln-99 has some great ones, but my favorite is Doug Judy

Doug Judy played by Craig Robinson is a good one. I also like The Vulture played by Dean Winters who is well known for his role as Mayhem in insurance commercials

Glaser also played himself as a bad guy of sorts on Louie, where he steals Louis C.K.’s joke about being a beekeeper with just one bee.

I’ll give a shout-out to Rachel Grate as Audra Levine from Crazy Ex-Girlfriend, a.k.a. one half of the greatest all-Jewish-female rap battle ever recorded:

Doug Judy and ‘The Vulture’ are two on-point examples of comedy foils, played by two great comedy actors.

Is the rest of the show as great as that? If so, I may have to seek it out on streaming.

Go for it - you won’t be sorry.