Mr. Burns' Blue-Haired Lawyer In The Simpsons Has A Donald Trump Connection
For a show filled with constant troublemakers, it makes sense that "The Simpsons" would feature multiple recurring lawyer characters. The most memorable is Lionel Hutz, the incompetent bozo who usually represents a member of the Simpson family; when he's taking on the case, that's a sure sign that whoever he's defending is going to jail. He's a familiar archetype, one we see echoes of with the incompetent alien chicken lawyer on "Futurama" or the perpetually anxious Ted on "Scrubs." Any lawyer who strays from the expected image of a smart, calculating, dignified man is always a welcome addition to a sitcom, but "The Simpsons" is unique in that it offers a counterpart.
Mr. Burns' lawyer, the blue-eyed New Yorker with the nasal voice, is the polar opposite of Lionel Hutz. He's an extremely efficient soulless drone, someone who tends to win his cases even if his methods aren't particularly ethical. He's never given a name, but he doesn't really need it; he's an unforgettable character, with a character design so distinct he's impossible to misplace.
So where did this guy come from? According to "Simpsons" writer Mike Reiss, he was inspired by Roy Cohn, an infamous dead-eyed 20th-century lawyer who helped fuel McCarthyism, was instrumental in the misconduct-marred trial and subsequent execution of the Rosenbergs, and defended Donald Trump during his many real-estate scandals in the '70s. As Reiss put it:
"Burns' lawyer, the nasty blue-haired guy in glasses, was inspired by Roy Cohn, the horrible man who sent the Rosenbergs to the electric chair and defended Donald Trump. (Why couldn't it be the other way around?) The Roy Cohn voice is done by Dan Castellaneta, one of his many spot-on impressions of obscure celebrities."
The Simpsons is a show that hates lawyers
Burns' blue-haired lawyer has slowly become the most prominent lawyer on the show, although not necessarily on his own merits. Lionel Hutz's character was retired after the classic era, for tragic real-life reasons: his voice actor, Phil Hartman (who also played Troy McClure) was murdered by his wife in 1998. Both characters' absences have been deeply felt in latter-day "Simpsons," as they've served as two of the show's main showcases for critiquing authority.
Troy McClure was the guy whose "educational" videos were always absurdly unhelpful and biased, and Hutz was the guy who proved that just because someone has a fancy law degree (or at least claims to have a fancy law degree) doesn't mean they're smart or reliable. And of course, who can forget that lovely moment when Hutz asks, "Can you imagine a world without lawyers?" and immediately imagines a harmonious utopia.
But as the blue-haired Roy Cohn impersonation took center stage, the show's main satirical aim towards lawyers took on a different shape. Rather than clumsy incompetence, this character operates with cold, ruthless efficiency. He's the type of lawyer to shut down a kids' lemonade stand on a technicality, or threaten Christmas carolers with a cease-and-desist order for copyright violations. It's still a smart approach for depicting bad lawyers, but it's not quite as fun as Hutz's "aww shucks" demeanor.
On the bright side, whenever the show needs an incompetent lawyer, they can always use poor ol' Gil Gunderson (also voiced by Dan Castellaneta) instead. That's what they did in season 13's "The Frying Game," to similarly bad results. It seems that whenever the Simpson family needs a lawyer, there will always be at least someone there to let them down in their hour of need.