The Simpsons is now in its 21st season, and while it is not the show it once was, I admit that I still sit down every Sunday night to watch it. I have seen every episode, in many cases more times then I can count. There are few things in my life more consistent then The Simpsons. When it starts, I was 7. I’m now 28. I can barely remember a time when The Simpsons was not a part of my life. So in celebration, I’m going to look back this week at The Simpsons. First the 10 best celebrity cameos not playing themselves. Then the best celebrity cameos playing themselves. And finally, my 10 favorite episodes of all time.
10. Donald Sutherland as Hollis Hurlbut
Sutherland is one of my favorite actors, as Hollis Hurlbut the head of the Springfield Historical Society; he makes a wonderful stuffy intellectual. At first he appears all kindness and good, but when his idol, Jebediah Springfield is questioned by Lisa, he tells her to get out “You are banned from this Historical Society. You and your children, and your children’s children. For three months”. Great stuff.
9. Johnny Cash as Space Coyote
I loved Johnny Cash, so to hear him turn up as a voice on The Simpsons was wonderful for me. To hear him as the voice of Homer’s spirit guide, in the guise of a coyote after he eats a really hot pepper, was even better. Cash was the perfect voice to play the part, as his deep voice lended seriousness to the character, which made it all the funnier when he tried to eat Homer’s pants.
8. Michele Pfeiffer as Mindy Simmons
In the great episode, “The Last Temptation of Homer”, Pfeiffer plays Mindy, the plant’s first female employee. She is drop dead gorgeous, but other than that she is pretty much the female version of Homer, loving everything that he does. Pfeiffer’s vocal work is funny, sexy and sympathetic. This is actually one of my favorite performances of all time for her, and she’s a great actress.
7. Albert Brooks as Cowboy Bob/Jacques/Brad Goodman/Hank Scorpio/Tab Spangler/Russ Cargill
I feel that I have to mention Albert Brooks here, because he was one the first major actors to do a voice on The Simpsons, as Cowboy Bob, the RV salesman and Jacques, the potential other man for Marge all the back in Season 1. He was great in both of those episodes, as he was as Brad Goodman, the self help guru, Tab Spangler, the guy who runs the fat camp and as Russ Cargill, the Presidential adviser in the movie. But it’s his work as Hank Scorpio, the madman bent on world domination that hires a clueless Homer that is really is greatest work. Genius work from a great actor.
6. Ricky Gervais as Charles Heatherbar
In one of the great late season episodes, Gervais plays Charles, the sad sack husband of a domineering wife, who trades spouses with Homer for an episode of Mother Flippers. Perhaps it’s no surprise that the episode is so good, as Gervais also wrote the episode. He falls in love with Marge because he is nice to him, writes her a gloriously dumb song. Gervais is hilarious in the role, making him a must have for this list.
5. John Waters as John
Waters is wonderful as the first gay person that Homer ever meets. Homer thinks John is the greatest guy he has ever met in his life, until he finds out he’s gay, and then he gets nervous that he is going to make Bart gay as well. Waters remains cheerful and funny throughout the episode, playing off of gay stereotypes, but also making John into a real person. Great work by a guy who is known more as a director than an actor.
4. Steve Martin as Ray Patterson
Martin is perfection as lowly civil servant Ray Patterson, the head of the sanitation department that Homer goes to war with. He seems like a perfectly reasonable guy that Homer simply goes off on for no reason, and then beats in an election because of his catchy song. Martin’s final notice is his last, as they vote to reinstate him and he gives a short speech “It gives me so much pleasure to leave you wallowing in the mess you’ve all created”, and the band plays him off. Great.
3. Dustin Hoffman as Mr. Bergstrom
Dustin Hoffman set the standard early for all Simpsons guest stars to follow. As Lisa’s substitute teacher, who inspires her and who she eventually develops a crush on, Hoffman is funny and touching. From his first appearance in a cowboy costume, to his final scene at the train station, Hoffman fills his role with humor and warmth. Despite the fact that Hoffman didn’t use his real name, there was never any doubt that it was providing that voice.
2. Kelsey Grammer as Sideshow Bob
It’s almost unfair to put Grammer on this list, since he has appeared 11 times over the years starting in the first season, and his most recent one being in Season 20. The Sideshow Bob episodes are some of the very best the series have ever done. In his first appearance, he tries to frame Krusty for robbery, then he tries to kill Selma, then he tries to kill Bart, then he runs for mayor, takes over an air show, works for his brother Cecil, tries to brainwash Bart into killing Krusty, helps Homer find who is trying to kill him, declares vendetta against the Simpsons after they out him in Italy, fakes his death to get at Bart and finally helps Bart and Lisa track down Homer’s real kidnapper. Grammer is perfect at Bob, his natural intelligence works for the evil genius, but he is also willing to look incredibly stupid at times, and has one of the most evil laughs in cartoon history. Despite all the years Grammer spent playing Frasier Crane, it will always be Sideshow Bob I think of when I think of him. 
1. Meryl Streep as Jessica Lovejoy
This will be a controversial choice for some people, especially since Grammer and Hoffman certainly get mentioned more often when great guest stars on The Simpsons are talked about. But Streep gets my vote for a very simple reason – every time I see the great episode that she is in, I cannot believe it is her doing the voice. She makes Jessica Lovejoy sound like a perfectly innocent little girl when she wants to be, and then an evil seductress later on. It is absolutely brilliant vocal work, and stands out to me as being the best guest role The Simpsons ever had. Genius.
10. Donald Sutherland as Hollis Hurlbut
Sutherland is one of my favorite actors, as Hollis Hurlbut the head of the Springfield Historical Society; he makes a wonderful stuffy intellectual. At first he appears all kindness and good, but when his idol, Jebediah Springfield is questioned by Lisa, he tells her to get out “You are banned from this Historical Society. You and your children, and your children’s children. For three months”. Great stuff.9. Johnny Cash as Space Coyote
I loved Johnny Cash, so to hear him turn up as a voice on The Simpsons was wonderful for me. To hear him as the voice of Homer’s spirit guide, in the guise of a coyote after he eats a really hot pepper, was even better. Cash was the perfect voice to play the part, as his deep voice lended seriousness to the character, which made it all the funnier when he tried to eat Homer’s pants.8. Michele Pfeiffer as Mindy Simmons
In the great episode, “The Last Temptation of Homer”, Pfeiffer plays Mindy, the plant’s first female employee. She is drop dead gorgeous, but other than that she is pretty much the female version of Homer, loving everything that he does. Pfeiffer’s vocal work is funny, sexy and sympathetic. This is actually one of my favorite performances of all time for her, and she’s a great actress.7. Albert Brooks as Cowboy Bob/Jacques/Brad Goodman/Hank Scorpio/Tab Spangler/Russ Cargill
I feel that I have to mention Albert Brooks here, because he was one the first major actors to do a voice on The Simpsons, as Cowboy Bob, the RV salesman and Jacques, the potential other man for Marge all the back in Season 1. He was great in both of those episodes, as he was as Brad Goodman, the self help guru, Tab Spangler, the guy who runs the fat camp and as Russ Cargill, the Presidential adviser in the movie. But it’s his work as Hank Scorpio, the madman bent on world domination that hires a clueless Homer that is really is greatest work. Genius work from a great actor.6. Ricky Gervais as Charles Heatherbar
In one of the great late season episodes, Gervais plays Charles, the sad sack husband of a domineering wife, who trades spouses with Homer for an episode of Mother Flippers. Perhaps it’s no surprise that the episode is so good, as Gervais also wrote the episode. He falls in love with Marge because he is nice to him, writes her a gloriously dumb song. Gervais is hilarious in the role, making him a must have for this list.5. John Waters as John
Waters is wonderful as the first gay person that Homer ever meets. Homer thinks John is the greatest guy he has ever met in his life, until he finds out he’s gay, and then he gets nervous that he is going to make Bart gay as well. Waters remains cheerful and funny throughout the episode, playing off of gay stereotypes, but also making John into a real person. Great work by a guy who is known more as a director than an actor.4. Steve Martin as Ray Patterson
Martin is perfection as lowly civil servant Ray Patterson, the head of the sanitation department that Homer goes to war with. He seems like a perfectly reasonable guy that Homer simply goes off on for no reason, and then beats in an election because of his catchy song. Martin’s final notice is his last, as they vote to reinstate him and he gives a short speech “It gives me so much pleasure to leave you wallowing in the mess you’ve all created”, and the band plays him off. Great.3. Dustin Hoffman as Mr. Bergstrom
Dustin Hoffman set the standard early for all Simpsons guest stars to follow. As Lisa’s substitute teacher, who inspires her and who she eventually develops a crush on, Hoffman is funny and touching. From his first appearance in a cowboy costume, to his final scene at the train station, Hoffman fills his role with humor and warmth. Despite the fact that Hoffman didn’t use his real name, there was never any doubt that it was providing that voice.2. Kelsey Grammer as Sideshow Bob
It’s almost unfair to put Grammer on this list, since he has appeared 11 times over the years starting in the first season, and his most recent one being in Season 20. The Sideshow Bob episodes are some of the very best the series have ever done. In his first appearance, he tries to frame Krusty for robbery, then he tries to kill Selma, then he tries to kill Bart, then he runs for mayor, takes over an air show, works for his brother Cecil, tries to brainwash Bart into killing Krusty, helps Homer find who is trying to kill him, declares vendetta against the Simpsons after they out him in Italy, fakes his death to get at Bart and finally helps Bart and Lisa track down Homer’s real kidnapper. Grammer is perfect at Bob, his natural intelligence works for the evil genius, but he is also willing to look incredibly stupid at times, and has one of the most evil laughs in cartoon history. Despite all the years Grammer spent playing Frasier Crane, it will always be Sideshow Bob I think of when I think of him. 
1. Meryl Streep as Jessica Lovejoy
This will be a controversial choice for some people, especially since Grammer and Hoffman certainly get mentioned more often when great guest stars on The Simpsons are talked about. But Streep gets my vote for a very simple reason – every time I see the great episode that she is in, I cannot believe it is her doing the voice. She makes Jessica Lovejoy sound like a perfectly innocent little girl when she wants to be, and then an evil seductress later on. It is absolutely brilliant vocal work, and stands out to me as being the best guest role The Simpsons ever had. Genius.
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