The show often contains dialogue that breaks the fourth wall. At the end of episode "Squid Pro Quo," Denny (William Shatner) ends the episode by saying, "I can't wait until next week." Alan Shore (James Spader) also notes that the show used to be on Mondays, and one time mentioned to Denny that "I've hardly seen you this episode." Melissa (Marisa Coughlan), Alan's assistant, once warns him against falling for a woman, citing, "She's only a guest star." There is even a case where television programs are discussed: "The only decent show is Boston..., oh, I can't say that. I'll break the fourth wall."
During the series, whenever Denny Crane (William Shatner) opens his cell phone it makes the same sound effect as the communicators from the original Star Trek series in which he played the role of Captain James T. Kirk.
Nearly all episodes (except season two, episode twenty-six, "Spring Fever," and several others in the first season) end with Denny and Alan sitting on the balcony, having a drink, smoking a cigar, and discussing the events of the episode.
David E. Kelley gave away the rights to the American adaptation of Life on Mars (2006), after making a failed pilot, in exchange for a final season of this show, with the minimum of episodes necessary for this show to achieve syndication.
Season five has an edited title music with added sound-effects matching the beat, including Jerry Espensen plopping & stamping with one foot on the floor, Carl Sack saying "whoops", Alan Shore tapping Denny Crane on his back, and Denny Crane firing a gun.
In one episode, Catherine Piper (Betty White) delivers cookies to a staff briefing, and says to Paul Lewiston (Rene Auberjonois) "My what an interesting face." This is likely a nod to Auberjonois' role on Star Trek: Deep Space Nine (1993) as Constable Odo; a shapeshifter who was never completely able to copy a human face, and thus always had a unique flat-looking face.
In addition to drawing on actors who shared a Star Trek history, the series also drew on the Murphy Brown bench strength. Leslie Jordon, Scott Bakula and Grant Shaud had all appeared with Candice Bergen in the 1990s.
The series was initially advertised as being titled "Fleet Street". These advertisements were seen during commercial breaks for The Practice (1997), which had several episodes that acted as a sort of pilot for the new series.
The firm's name is Crane, Poole, and Schmidt. The firm, according to its "website" was firmed in 1984. Ed Kranepool was a baseball player, who retired in 1979. Mike Schmidt was a baseball player who retired in 1989. The midpoint of the retirements is 1984. Kranepool and Schmidt sounds like Crane, Poole, and Schmidt.
Henry Gibson, who plays Judge Clark Brown, once appeared on Knight Rider as a character named Donald Crane. Coincidentially, Freddie Prinze Jr. plays Donald "Donny" Crane, the son of Denny Crane, in Boston Legal.
The trivia items below may give away important plot points.
Denny Crane has never lost a trial. According to season one, episode twelve, "From Whence We Came", he has won six thousand forty-three trials in forty-five years. This makes a minimum of 11 cases a month. The achieved amount of money isn't imaginable, but must have passed the 50.000.000,- mark easily.
At the end of season two, Denny Crane has shot four people. (1) The man who threatened to kill Alan, because he helped his ex-wife not to have their children kidnapped by him, (2) the rapist, who killed a girl, (3) the homeless man, who threw a rock at him, and (4) his therapist. Actually, he shot his therapist twice, once in a session when he threatened to kill him, and once in the courtroom, when he was again threatening to kill him.
In Season 1, Denny Crane once calls Alan Shore "his husband". As it was surely not worked out by the writers at that time, this is the exact thing, that is going to happen in the series finale, when the two men marry each other.
Henry Gibson, who plays Judge Clark Brown, has the most interactions in court with lawyers from Crane, Poole & Schmidt, and is a client one time. With a sum of 24 episodes, Clark Brown is the most frequented Judge in Boston courtyard.