The 20 best Simpsons guest stars

In no particular order…

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Phil Hartman

The late, great Phil Hartman voiced some of my favourite characters on the show, the most well-known probably being Troy McClure and Lionel Hutz. Known for his work on Saturday Night Live and appearances in film and TV, Hartman brought so much to The Simpsons, and after his death a noticeable void was left in the show. He said of his multiple appearances: “It’s the one thing that I do in my life that’s almost an avocation. I do it for the pure love of it”…and you can hear the passion and glee in his performances, which is perhaps why his are some of the best on the show.

Kelsey Grammer

No matter how far downhill The Simpsons has gone in recent years, there are two kinds of episodes I will always watch and enjoy: Sideshow Bob episodes and Treehouse of Horror episodes. Sideshow Bob is an extremely well-written and well-acted character, and we have Frasier star Kelsey Grammer to thank for that. Grammer already has a pretty brilliant voice, and just turns it up a notch for playing Bob. He is a superb villain – to me, the most memorable of his performances is in the episode Cape Feare – who else could make the sound of stepping on rakes so hilarious?

Albert Brookstumblr_kzw1dlEZjW1qzieq2o1_400

I’ve had the joy of being exposed to a lot more Albert Brooks this year, mainly thanks to his brilliant performance in 2011’s Drive. It took me a while to discover that Bernie Rose was played by the same actor that voiced possibly my all-time favourite character in The Simpsons, super-villain Hank Scorpio. He has made a few other enjoyable appearances in the show as well as The Simpsons Movie, but he will always be Scorpio to me. Like Phil Hartman, you can hear the fun that Brooks is having, and we get to share in it. Not much more needs to be said about this great man. Perfect character and perfect episode.

Dustin Hoffman 

Lisa’s Substitute is an episode that gives me a lump in my throat, and only a few Simpsons episodes do this. This is largely thanks to Dustin Hoffman’s performance as substitute teacher Mr Bergstrom, a kind, gentle and passionate character portrayed brilliantly by a brilliant actor. It is also Yeardley Smith’s chemistry with Hoffman that makes the episode stand out to me, and that’s the great thing about the regular voice cast on the show – pair them up with the right co-star and you get an episode that is not just funny, but touching.

Michelle Pfeiffertumblr_m0ohwtiOYT1qfooc3

The Last Temptation of Homer is quite a serious episode, dealing with the not-very-funny subject of infidelity. Luckily the writers are able to tackle serious matters while still retaining some humour, and so are the actors. Michelle Pfeiffer was brought in to play Homer’s temptress, Mindy Simmons. If you listen to the commentary on the episode, it’s pointed out that rather than playing her as a flirtatious seductress, Pfeiffer just acts ‘normal’, in no way trying to tempt Homer. It’s just a very real situation, of two compatible people trying to resist each other in the workplace, and Pfeiffer fits into this perfectly (and does an excellent Homer ‘drool’ noise).

Joe Mantegna

I can’t imagine anyone other than Joe Mantegna playing gang leader Fat Tony, it is a performance that is suitably scary and funny. His background in film and TV often playing ‘funny gangsters’ makes him the perfect actor to play this character, and you can see why the writers brought him back again and again.

Kathleen Turner23456372123300-31165500

I find Stacy Lovell, the inspiration for Malibu Stacy, a funny character to start with – she’s a drunken has-been with a string of lovers living in Stacy’s Dream House. But Kathleen Turner makes it even better by just being hilarious. She’s showed that she’s a great comedienne in the dark John Waters comedy Serial Mom, and like Waters, she fits into the Simpsons world seamlessly.

James Woods

James Woods is great at playing James Woods. In Homer and Apu, he takes over the running of the Kwik E Mart in preparation for a movie role and brings the perfect amount of frankness, arrogance and comedic timing. He’s reprised his ‘role’ of James Woods in Family Guy, continuing to show how well he works as a voice actor.

Winona Ryder

I had to include Winona Ryder for purely selfish reasons – being that Lisa’s Rival is one of my favourite ‘Lisa’ episodes. It’s often difficult for adults to effectively portray a child’s voice, but Ryder does it flawlessly and subtly. And again, she works well alongside Yeardley Smith, turning a character that could be quite annoying into something more.

John Waterstumblr_lgue41QDq61qh8t3yo1_500

I am a massive John Waters fan, not just because of his style of cult filmmaking, but because he seems like such a nice guy. And this comes through in his performance (he is pretty much playing himself as a shop owner). He fits seamlessly into The Simpsons world, and the subject of homosexuality and homophobia is tackled openly and frankly, largely thanks to him and Dan Castellaneta playing off eachother. Genius.

Anne Bancroft 

The Graduate is one of my all-time favourite movies, so naturally I think Anne Bancroft in The Simpsons is brilliant. Her comic timing is surprisingly very good for quite an underplayed character, a Doctor helping Marge conquer her fear of flying. It’s subtle, but still very funny – and works really well with the animation and writing style.

Patrick Stewart 

Homer the Great is a classic in Simpsons writing history. And Patrick Stewart is a classic British actor and also brilliant voice actor (see: American Dad). So put the two together and you have perfection. Stewart’s booming, Shakespearean voice is superb at delivering comedic lines and as usual, he’s entertaining from start to finish. “Now let’s all get drunk and play ping pong!”

Lawrence Tierneytumblr_ls5vuwfrby1qzdsi5o1_500

Marge Be Not Proud is a favourite episode of mine, and Reservoir Dogs actor Lawrence Tierney gives his wonderfully gravelly, dirty voice playing a security guard. The realism of this episode is very well written, a kid being caught stealing – and Tierney is suitably scary and imposing. The character also comes out with some odd mannerisms (“Capiche?”) and his voice sounds great delivering them.

Donald Sutherland 

Donald Sutherland has one of the best voices in Hollywood. I could listen to him all day; to me he’s on par with Morgan Freeman. So to be honest, any character he played in The Simpsons I would love. And his performance as a museum curator doesn’t disappoint – again it’s another one that works so well thanks to the main voice cast and Sutherland’s adaptability.

Johnny Cashspace-coyote

The coyote in El Viaje Misterioso de Nuestro Jomer has become somewhat of a cult icon in Simpsons world. I’ve seen tattoos of him – that is the effect he has. This may just be because the episode itself is quite iconic, completely subverting conventions visually and within the narrative. But Johnny Cash gives a superb performance as Homer’s spirit guide, partly because his voice is just awesome, but also because he is extremely funny and grounded for such an odd character.

Steve Martin 

Steve Martin is always going to give a great ‘angry man’ performance, and is perfect for the role of Ray Patterson, Springfield’s sanitation commissioner who is overthrown by Homer. He is one of those characters who is brought in mainly to comment on the fact that Homer is a complete idiot, and yet the townspeople are oblivious to this (see: Frank Grimes). And he does it so well that you may not even notice that it is Steve Martin, and to me that’s always the mark of a great performance; when the actor does not overshadow the role.

Ron Howard

It’s always great when a guest actor is not afraid to poke fun at themselves. Ron Howard, playing himself, isn’t portrayed in the best light – often angry, alcoholic and plagiarising. When You Dish Upon a Star is an episode exploring the vanity and fakery of Hollywood and Ron Howard plays into this perfectly. His deadpan delivery of the line: “Homer! We’re out of vodka.” will always be one of my favourites.

David Hyde Pierce tumblr_mdl21xAUOU1rw41szo1_500

David Hyde Pierce plays Cecil, brother of Kelsey Grammer’s Sideshow Bob, and of course the two play off each other brilliantly. Cecil is quite a gentle character (apart from being slightly evil) and Bob is, of course, very angry – so the two give a great joint performance. It’s even better that in this episode, Cecil turns out to be the villain and Bob is actually good. It’s just another direction that Bob is taken in, and Pierce works alongside him like a pro.

Mark Hamill

I love Mark Hamill. Who doesn’t? I mean, Star Wars, obviously – but I love him even more for his voice acting. He’s most notably played the Joker in Batman: The Animated Series, and plays Skips and others in Regular Show, but in The Simpsons he’s mainly playing Mark Hamill. And again, he’s another actor who’s not afraid to poke fun at himself and the franchise that made him famous.

Tom Hanks7378-27066

I wasn’t a massive fan of The Simpsons Movie – it had its moments, and some great voice acting, but was far from the show that I grew up watching. However, the very brief appearance of Tom Hanks made me laugh profusely. Any appearance by Tom Hanks will brighten my day, so I had to include him on this list for restoring my faith in the ‘new’ Simpsons. Thanks Tom!

This was an extremely difficult list to narrow down. So the runners up are…

Paul & Linda McCartney, Barry White, Luke Perry, George Harrison, Rodney Dangerfield, Jack Lemmon, Martin Sheen, Jim Varney, U2, Pierce Brosnan, Ramones, Spinal Tap, Gillian Anderson & David Duchovny, Helen Hunt, Jane Kaczmarek, George Carlin & Martin Mull, Ernest Borgnine, Stephen Hawking, Penn & Teller, Lisa Kudrow.

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