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The Simpsons (1989-present)
Azaria became most famous for his voice work on the animated television show The Simpsons, a show that continues to the present. He joined the show having previously performed only one voice over: as the titular animated dog in the failed Fox pilot Hollywood Dog, a show he described as "sort of Roger Rabbit-esque, where the dog was animated but everybody else was real." The first voice he performed on The Simpsons was that of town bartender Moe Szyslak, replacing Christopher Collins who had initially recorded the character's voice. Having known him from Hollywood Dog, casting director Bonita Pietila called Azaria and asked him to audition for the voice of Moe. At the time he was performing the role of a drug dealer in a play, utilizing a voice based on the actor Al Pacino's performance in the film Dog Day Afternoon. He used the voice in his audition for The Simpsons and, on the request of the show's executive producers Matt Groening and Sam Simon, made the voice more gravelly. Groening and Simon thought the resultant voice was ideal for Moe and took Azaria over to the Fox recording studio. Before he had even seen a script, he recorded several lines of dialogue as Moe for the episode "Some Enchanted Evening", dubbing Collins' voice. Azaria did not expect to hear from the show again but they continued to call him back, first to perform the voice of Chief Wiggum, and then Apu Nahasapeemapetilon. By the show's second season he was performing multiple recurring voices and so was given a contract and made a permanent member of the main cast. As he joined later than the rest of the cast, Groening still considers Azaria the "new guy." In addition to Moe, Wiggum and Apu, Azaria provides the voices of the Comic Book Guy, Carl Carlson, Cletus Spuckler, Professor Frink, Dr. Nick Riviera, Lou, Snake, Kirk Van Houten, the Sea Captain, Superintendent Chalmers, Disco Stu, Duffman, the Wiseguy and numerous other one-time characters.

In addition to Moe's voice being based on Al Pacino, many of Azaria's other recurring characters are based on an existing source. He took Apu's voice from the many Indian and Pakistani convenience store workers in Los Angeles that he had interacted with when he first moved to the area, and also loosely based it on Peter Sellers' character Hrundi V. Bakshi from the film The Party. Originally, it was thought that Apu being Indian was too offensive and stereotypical, but due to Azaria's reading of the line "Hello, Mr. Homer", which the show's producers thought was hilarious, his character stayed. Azaria, however, disputed this on LateNet with Ray Ellin, claiming that Apu was always intended to be stereotypical. Chief Wiggum's voice was originally a parody of David Brinkley but when Azaria was told it was too slow he switched it to that of Edward G. Robinson. Officer Lou is based on Sylvester Stallone, and Dr. Nick is "a bad Ricky Ricardo impression." The "Wise Guy" voice is "basically Charles Bronson," while Carl is "a silly voice [Azaria] always did." Two of the voices come from his time at college: Snake's is based on Azaria's old college roommate, while Comic Book Guy's voice is based on a student who lived in the room next door to Azaria's, who went by the name "F". Professor Frink is based on Jerry Lewis's performance in the original The Nutty Professor, and the Sea Captain's is based on English actor Robert Newton's portrayal of many pirates. Azaria based his performance for the one-time character Frank Grimes, from the episode "Homer's Enemy", on actor William H. Macy. He counts Grimes as the hardest, most emotional performance he has ever had to give in the history of The Simpsons.

Azaria's work on the show has won him three Emmy Awards for Outstanding Voice-Over Performance, in 1998, 2001 and 2003. He was also nominated for the award in 2009 and 2010, but lost to co-star Dan Castellaneta and guest star Anne Hathaway respectively. Azaria, with the rest of the principal cast, reprised all of his voice roles from The Simpsons, for the 2007 film The Simpsons Movie. Azaria notes that he spends "an embarrassingly small amount of time working on The Simpsons." He works for "an hour on Thursdays when we read through the script, then four hours on Monday when we record it, and I'll pop in again once or twice." He concludes it is "the best job in the world, as far as I'm concerned."

Azaria earns around US$300,000 per episode of The Simpsons. Up until 1998, Azaria was paid $30,000 per episode. Azaria and the five other main The Simpsons voice actors were then involved in a pay dispute in which Fox threatened to replace them with new actors and went as far as preparing for casting of new voices. However, the issue was soon resolved and from 1998 to 2004, they received $125,000 per episode. In 2004, the voice actors intentionally skipped several table reads, demanding they be paid $360,000 per episode. The strike was resolved a month later, with Azaria's pay increasing to something between $250,000 and $360,000 per episode. In 2008, production for the twentieth season was put on hold due to new contract negotiations with the voice actors, who wanted a "healthy bump" in salary. The dispute was later resolved and Azaria and the rest of the cast received their requested pay raise: approximately $400,000 per episode. Three years later, with Fox threatening to cancel the series unless production costs were cut, Azaria and the other cast members accepted a 30 percent pay cut, down to just over $300,000 per episode.

Television work
With the continuing success of The Simpsons, Azaria began taking on other, principally live-action, roles. His The Simpsons co-star Nancy Cartwright wrote that: "The thing about Hank that I most remember is that he started out so unassuming and then, little by little, his abilities were revealed and his contributions to the show escalated. I realized Hank was going to be our breakaway star." He was a main cast member on the show Herman's Head (1991-1994) playing Jay Nichols, alongside The Simpsons co-star Yeardley Smith. He regularly recorded for The Simpsons and filmed Herman's Head during the same day. In 1994 he made his first appearance on the sitcom Friends, playing the recurring character David, one of Phoebe Buffay's boyfriends. His first appearance was in the show's tenth episode, before the character left for Minsk. He came back in the show's seventh season (2001), before making several appearances in the ninth (2003), which culminated in David proposing to Phoebe. She rejected him, and David left the show for good. From 1995 to 1999, Azaria had a recurring role in the sitcom Mad About You as Nat Ostertag, the dog walker. Azaria was nominated for the Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series for his roles in both Mad About You (in 1998) and Friends (in 2003). Azaria had the lead role in the short-lived sitcom If Not For You in 1995, playing record producer Craig Schaeffer.

Azaria created and starred in the sitcom Imagine That in 2002, replacing Emeril mid-season in the NBC lineup. He played Josh Miller, a comedy writer, who "transformed" each episode into a character Miller has imagined, "provid[ing] a humorous outlet for his frustrations at home and work". Production closed after five episodes and it was canceled after just two aired, due to poor critical reaction and ratings. Azaria later commented on the show "I wanted to do something really truthful and interesting and impactful. We had a bunch of executives sitting in the room, all agreeing that The Larry Sanders Show was our favorite thing on television, but we couldn't do it on NBC, and nor would we want to from a business standpoint; it simply wouldn't make enough money. By the time it aired, the writing was sort of on the wall, and I don't blame them at all. It was apparent it wasn't working."

Azaria starred as psychiatrist Craig "Huff" Huffstodt in the television series Huff, which ran for two seasons between 2004 and 2006, airing 24 episodes. Azaria enjoyed working on the show and by the second season began "to extend [his] character emotionally," and "he really is beginning to unravel." Azaria served as an executive producer on the show and directed an episode of its second season. After reading the pilot script he sent it to Platt, who took the role of Huff's friend, Russell Tupper. Gillian Flynn of Entertainment Weekly called Azaria "impressively subtle" in the role, while John Leonard of New York said he was a "shrewd bit of casting." The show garnered seven Emmy nominations in 2005 including a nomination for Azaria for Outstanding Lead Actor in a Drama Series. Despite the awards, the show continually received low ratings and Showtime chose not to commission it for a third season.

Azaria returned to live-action television in 2011, starring in the NBC sitcom Free Agents, a remake of the British series of the same name. He plays Alex, a recently divorced public relations executive "who is missing his kids and trying to keep himself together," and ends up sleeping with a co-worker (Kathryn Hahn). Azaria was apprehensive about the project, disliking the lengthy schedule required of a lead actor in a single-camera series, and favoring the "sensibility" of cable shows. However, he liked the script and executive produder John Enbom's previous series Party Down and decided to accept the part. Despite Azaria mounting a campaign on Twitter to save it, the series was canceled after four episodes due to low ratings.

Film work
His first theatrically released feature film appearance was in the 1990 film Pretty Woman, where he played a police detective investigating the murder of a prostitute. He played television producer Albert Freedman in the 1994 Academy Award-nominated film Quiz Show. In 1996, Azaria played gay Guatemalan housekeeper Agador Spartacus in the film The Birdcage. He was nominated for the Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Supporting Role, and critically branded "the most hilarious performance in the film," by Alison Macor of The Austin Chronicle, while Empire wrote that he "[stole] the show." For the role he used a Guatemalan accent, and made himself sound as effeminate as possible. He had chosen two possible voices, an effeminate one and a tougher one. After advice from a drag queen, he chose the effeminate voice. Three weeks into production, he realized he sounded exactly like his grandmother, which aided his performance. Azaria appeared in numerous other films in the late 1990s, including Heat (1995), Grosse Pointe Blank (1997) and Celebrity (1998), as well as playing photographer Victor "Animal" Palotti in the 1998 film Godzilla. He went on to appear opposite Gwyneth Paltrow, as Walter Plane, in the 1998 adaptation of Great Expectations. In 1999, he starred in Disney's Mystery, Alaska as Charles Danner, and Universal Pictures's Mystery Men, as the superhero The Blue Raja. Other film roles included Hector Gorgonzolas in America's Sweethearts (2001), Claude in Along Came Polly (2004), and the young Patches O'Houlihan in Dodgeball: A True Underdog Story (2004), the latter two with Ben Stiller. For his role of Claude, a French scuba instructor, in Along Came Polly, Azaria donned a wig and worked out "for seven or eight weeks," to get into the physical shape the part required. He also appeared as Professor Groteschele in Fail Safe (2000), a production that was broadcast live.

Azaria played composer Marc Blitzstein in Tim Robbins' film Cradle Will Rock in 1999. Paul Clinton wrote that Azaria was "brilliant as the tortured (is there any other kind) artist Blitzstein." The same year he appeared as author and journalist Mitch Albom alongside Jack Lemmon in the television film Tuesdays with Morrie, winning the Primetime Emmy Award for Outstanding Supporting Actor in a Miniseries or a Movie for the role. Azaria described the latter as the "best work [he has] done." These were two of the first dramatic roles Azaria had taken; throughout his career Azaria has primarily worked in comedy, but tries to balance the two. Azaria commented: "all the roles I got were in comedy at first, and I was certainly happy to get those, so I never felt the lack of being considered a dramatic actor because I was so happy to get what I got. And then I became surprised later on when I got dramatic roles. But I never went, 'OK, now it's time to get a dramatic role.'" His next dramatic role was in the television film Uprising in 2001. The film was based on the 1943 Warsaw Ghetto Uprising and Azaria played Mordechaj Anielewicz, one of the revolt's leaders. Azaria was confused by his casting in Uprising and frequently asked the film's producer and director Jon Avnet as to why he was selected. "I know [Avnet] liked the fact I was Jewish, and he knew I could do accents well. He cast me and David Schwimmer in [Uprising], and we were both sort of mystified. He had some instinct that he wanted people who were more known for being funny. He never explained it satisfactorily to me; I don't understand why." His parts in Tuesdays With Morrie and Uprising affected him, causing a depressive state which he countered with DVDs of the comedy series Monty Python. Azaria found Uprising to be "very difficult very depressing very emotionally challenging," material. In 2003, Azaria played journalist Michael Kelly, the former editor of The New Republic, in the drama film Shattered Glass. Kelly died a few months before the film was released and Azaria said the film "has become a weird kind of eulogy to him."

Azaria has made multiple film appearances since Huff end in 2006. He appeared as a smooth-talking American named Whit in David Schwimmer's directorial debut Run Fatboy Run. During production he became good friends with co-star Simon Pegg, performing The Simpsons voices on request, frequently distracting Pegg when he was supposed to be filming. He worked with Stiller again on 2009's Night at the Museum: Battle of the Smithsonian in which Azaria played the villainous pharaoh Kah Mun Rah, utilizing a Boris Karloff accent. Although the film received mixed reviews, critics praised Azaria's performance. Perry Seibert of TV Guide wrote that "thanks to Azaria, a master of comic timing. His grandiose, yet slightly fey bad guy is equally funny when he's chewing out minions as he is when deliberating if Oscar the Grouch and Darth Vader are evil enough to join his team." He appeared as Abraham in Year One, and as Dr. Knight in 2010's Love and Other Drugs.

Azaria starred as Gargamel in the live-action adaptation of The Smurfs in 2011. Azaria wore a prosthetic nose, ears, buck teeth, eyebrows and a wig, as well as shaving his head; spent approximately 130 hours in the make-up chair over the course of the production. Azaria considered Gargamel's voice to be the most important part of his performance. The producers wanted an "old, failed, Shakespearean actor" voice, but Azaria felt this would lack energy and wanted something more Eastern European. He eventually selected a voice similar to that of Paul Winchell's from the cartoon. Azaria disliked the cartoon when it first aired, and considered Gargamel too one-dimensional a character and "just this straight villain"; he opted to make Gargamel "more sarcastic" than in the cartoon, but "discovered that there's no way to play Gargamel without screaming your head off at certain points — ramping him up and getting him very upset over Smurfs." He interpreted him as "very lonely", adding that "he hates the Smurfs because they're such a happy family. He wants in really badly. I think he wants to be embraced as a Smurf." Azaria worked with the writers to "infuse" the script with some of his ideas about the character, "particularly with the 'married' relationship between Gargamel and [his cat] Azreal [sic]" which Azaria conceived. Scott Bowles of USA Today called Azaria the "human standout"; Betsy Sharkey of The Los Angeles Times felt he suffered the "greatest disservice" of the film's cast due to a poor script.

Further voice work
Azaria has performed a number of voice roles in addition to his work on The Simpsons, although he noted in 2005: "I started doing other voiceovers for cartoons for a couple of years, but I didn't really love it. I was spoiled by The Simpsons." He voiced Venom/Eddie Brock in Spider-Man: The Animated Series for four years between 1994 and 1996, and in the animated feature Anastasia (1997), as Bartok the bat, reprising the role in the direct-to-video sequel Bartok the Magnificent (1999). He also voiced Eric in the American dub of the series Stressed Eric, and Harold Zoid in the 2001 Futurama episode "That's Lobstertainment!".

Azaria provided the voices for the characters Carlos and Phil in Hop (2011). The response to the film was mostly negative, but many reviewers praised Azaria's performance. For example, Sandie Chen of The Washington Post said "Azaria has been honing his over-the-top Spanish accent since The Birdcage, so anything he says grabs some laughs," while Emma Simmonds of Time Out called him an "unflappable presence, voicing two characters with style." Later in the year he voiced The Mighty Sven in Happy Feet 2.

Once The Simpsons was "going steadily" and Azaria had enough money to live on, he stopped working on commercials as he found them "so demoralizing" and he always sounded sarcastic whenever he read for them. When recording the part of "Jell-O Man" for a Jell-O commercial, he was told to make the voice he offered "more likeable and friendly so that children like him." After pointing out that "Jell-O Man" was a fictional character, he left and never recorded for an advertisement again.

Directing and theatrical work
Azaria wrote and directed the 2004 short film Nobody's Perfect, which won the "Film Discovery Jury Award for Best Short" at the US Comedy Arts Festival. In January 2007, he was confirmed to be directing Outsourced, a film about two American workers who journey to get their jobs back, after their factory is moved to Mexico. However, in 2009, Azaria told Empire he was now focusing on making a documentary about fatherhood. Two years later he told The Los Angeles Times that the project was "half-complete" and is "forever looking for financing to finish it."

Azaria has appeared in several theatre productions. In 2003 he appeared as Bernard in a run of David Mamet's play Sexual Perversity in Chicago, along with Matthew Perry and Minnie Driver, in London's West End. In 2004, Azaria began appearing as Sir Lancelot, the French Taunter, and four other characters in Spamalot, the musical version of Monty Python and the Holy Grail, which opened in Chicago in December 2004 before moving to the Shubert Theatre on Broadway. The show was met with critical acclaim, receiving fourteen Tony Award nominations in 2005, with Azaria being nominated for Best Performance by a Leading Actor in a Musical. Azaria described it as "the most fun that I've ever had in my entire life." Reuniting with The Birdcage director Mike Nichols and being a huge Monty Python fan, he saw it as an opportunity he could not pass up, describing it as "so much fun that I haven't realized how tiring it is." He took a break from the show in June 2005, with Alan Tudyk filling in for him, to work on Huff, but returned in December 2005. Continuing his theater roles, in late 2007 he starred in Aaron Sorkin's The Farnsworth Invention, playing RCA head David Sarnoff.