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.

The ringtone of Catherine Piper (Betty White) is the opening theme of David E. Kelly's other show The Practice (1997), of which this show is spun-off.

James Spader (Alan Shore) and William Shatner (Denny Crane) are the only cast members to appear in every episode of the series.

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.

Regular cast members William Shatner, Rene Auberjonois, and John Larroquette have all appeared in the Star Trek franchise. Several other former Star Trek cast members have guest-starred in the show: Armin Shimerman, Jeri Ryan, Ethan Phillips, Michelle Forbes, Scott Bakula, and Lee Duncan. Lesser "speaking" roles were held by Ellen Bry, David Clennon, Michael Wiseman, Ron Ostrow, Alan Ruck, Derek Magyar, and Lawrence Pressman.

James Spader was born in Boston, Massachusetts.

Denny Crane is a major conservative, whereas Alan Shore is a major liberal. Denny Crane often shoots liberals with paintball guns.

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.

William Shatner and Candice Bergen appeared in Miss Congeniality (2000).

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.

Brian Waller, Arne Starr, and Jason Brooks went on from this show to appear in Star Trek (2009).

Lake Bell quit the show during season one to star in Surface (2005). After the show was cancelled, Bell did some guest appearances in season three.

Before becoming a regular cast member, Rene Auberjonois guest-starred in most episodes of the first half of season one.

Despite being a senior partner at the firm, Paul Lewiston (Rene Auberjonois) is rarely seen in a courtroom, and even less often has dialogue when seen there.

William Shatner and John Larroquette appeared in Star Trek III: The Search for Spock (1984).

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.

Multiple actors and actresses from every Star Trek generation and television series appeared on this show, but only one from Star Trek: Enterprise (2001), Scott Bakula.

William Shatner and Rene Auberjonois appeared in Nicholas Meyer's Director's Cut of Star Trek VI: The Undiscovered Country (1991).

Lake Bell (Sally) claims her audition for the role was unsuccessful.

The list of actors and actresses that held "lesser" roles in a production of the Star Trek franchise includes Bill Blair, Tom Knickerbocker, Lorna Raver, Mark Moses, Kelly Connell, Gregory Itzin, and Dennis Cockrum.

Craig Bierko (Jeffrey Coho) & Constance Zimmer (Claire Simms) also worked together on UnREAL (2015) as Chet Wilton & Quinn King respectively.

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.

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.

Denny Crane was married six times (including his very brief marriage in season two). In the series-finale, Denny Crane marries Alan Shore, what brings his marry-count to 7.

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.