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50 free Boston Legal trivia questions with answers — trivia quiz, new questions added Aug 2026.
Boston Legal ran for five seasons and 101 episodes, won Emmys for James Spader and William Shatner, and ended with Denny Crane and Alan Shore getting married on a balcony. It began as a spin-off of The Practice with the working title Fleet Street, and its law firm building was really on Boylston Street. This Boston Legal quiz covers the lawyers of Crane, Poole & Schmidt, their quirks and cases, the guest stars from Betty White to Michael J. Fox, David E. Kelley's other shows and the awards the series collected. Every answer is sourced and explained.
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Q 01Boston Legal is a direct spin-off of which earlier legal drama?
The Practice
Alan Shore, Denny Crane, Tara Wilson and Sally Heep all carried over from The Practice's eighth and final season in 2004.
Q 02What is the name of the law firm at the centre of Boston Legal?
Crane, Poole & Schmidt
The other three are also Kelley firms: from Ally McBeal, The Practice and L.A. Law respectively. Edwin Poole, the middle name, appears in only four episodes.
Q 03On which network did Boston Legal air from 2004 to 2008?
ABC
It was produced with 20th Century Fox Television but ran on ABC, which put it on hiatus in its first season to make room for a new show called Grey's Anatomy.
Q 04Which two things do Alan and Denny share on the balcony at the end of most episodes?
Cigars and scotch
The balcony musings became the show's signature, a space for two political opposites who happen to be best friends.
Q 05What was the show's working title, an allusion to where the firm had its offices?
Fleet Street
It was briefly The Practice: Fleet Street. The real building used as the office is at 500 Boylston Street, 1.4 miles away.
Q 06Denny Crane blames his lapses on what illness, though he is really in the early stages of Alzheimer's?
Mad cow disease
He claims to have never lost a case in fifty years of practice, and by season three mostly appears in court as a plaintiff or defendant because of his own antics.
Q 07What happens between Denny and Alan in the series finale?
They get married
The wedding let Denny pass his fortune to Alan and gave Alan the power to make his medical decisions. Shirley and Carl married in the same episode.
Q 08Which real Supreme Court justice officiates Shirley and Carl's finale wedding at Nimmo Bay?
Antonin Scalia
Carl Sack, an old flame, had proposed to Shirley in the episode 'Thanksgiving'. The double wedding was the show's last scene.
Q 09How many episodes of Boston Legal aired in total?
101
The 13-episode final season was ordered specifically to push the show past the 100-episode mark that makes syndication viable.
Q 10How many Primetime Emmy nominations did Boston Legal receive over its run?
26
They included Outstanding Drama Series nods in 2007 and 2008. Its seven nominations in 2008 were a series high.
Q 11How many Emmys for Outstanding Lead Actor in a Drama did James Spader win as Alan Shore?
Three
The first, in 2004, came for The Practice; the 2005 and 2007 wins were for Boston Legal, beating the likes of Hugh Laurie and Kiefer Sutherland.
Q 12William Shatner's Denny Crane won him an Emmy for each series. Which other award did he win for the role in 2005?
A Golden Globe
Critic Pat Jordan described the performance as 'William Shatner the man playing William Shatner the character playing Denny Crane, who was playing William Shatner'.
Q 13Which senior partner did Candice Bergen join the show to play in January 2005?
Shirley Schmidt
Q 21Which British barrister and creator of Rumpole of the Bailey was hired as a consultant on the show?
John Mortimer
Mortimer's Rumpole was another shabby, wine-loving advocate with a taste for lost causes, a clear cousin of Alan Shore.
Q 22Which new ABC hit pushed Boston Legal onto hiatus during its first season in 2005?
Grey's Anatomy
Boston Legal came back that autumn with an extended 27-episode second season.
Q 23The show was noted for frequently doing what, unusual for a legal drama?
Breaking the fourth wall
Characters joked about being on television, their time slot and even the show's own cancellation, especially Denny and Alan on the balcony.
She arrived in episode 11 of season one and stayed to the end. Bergen had already won five Emmys as Murphy Brown.
Q 14What nickname do the other lawyers give Jerry Espenson because of how he walks?
Hands
He walks with his palms pressed to his thighs, purrs when anxious, hops when excited and shouts 'Bingo!' as a yes. Christian Clemenson won a 2006 Emmy for the part.
Q 15Jerry Espenson is an attorney diagnosed with which condition?
Asperger syndrome
Clemenson was nominated for three Emmys for the role and won Outstanding Guest Actor in a Drama in 2006 before being promoted to the main cast.
Q 16Which actor joined in season four as Carl Sack, a senior partner transferred from the New York office?
John Larroquette
Larroquette had won four straight Emmys as Dan Fielding on Night Court. Tara Summers joined at the same time as associate Katie Lloyd.
Q 17Betty White's recurring character, Alan's blackmailing former assistant, was called what?
Catherine Piper
She first played the church-going gossip on The Practice in 2004 and appeared in 16 episodes of Boston Legal, befriending the matricidal Bernard Ferrion.
Q 18Leslie Jordan's character Bernard Ferrion hired Alan after killing his mother with what?
A frying pan
Catherine Piper took the short-statured murderer under her wing to introduce him to God. He appeared in six episodes.
Q 19Alan Shore suffers from night terrors and a fear of what?
Clowns
He also gave up having a home, preferring to live in hotels. He hired Betty White's replacement partly to help with the night terrors.
Q 20Which creator of Boston Legal was himself a former lawyer and Boston native?
David E. Kelley
Kelley captained Princeton's ice hockey team before law school, and married Michelle Pfeiffer after a blind date in 1993.
Q 24Which prestigious broadcasting honour did Boston Legal win in 2005?
A Peabody Award
Nielsen also found it drew the richest audience on television, measured by high-income viewers aged 18 to 49.
Q 25René Auberjonois, who played Paul Lewiston, was famous for which Star Trek role?
Odo
He played the shape-shifting security chief on Deep Space Nine, was an Emmy nominee for Benson, and voiced Chef Louis in The Little Mermaid.
Q 26Paul Lewiston has his meth-addicted daughter Rachel abducted and sent where?
A rehab centre
He takes custody of her daughter Fiona, his granddaughter. Paul is the firm's expert on Far Eastern markets.
Q 27Brad Chase often relies on his background in which military branch to intimidate people?
Marine Corps
Mark Valley, who played him, really did graduate from West Point with a maths degree in 1987.
Q 28Where does Denny marry Brad Chase and his pregnant bride moments before their baby is born?
A hospital labour room
Denise had gone into labour at her own wedding, and Brad insisted no child of his would be born out of wedlock.
Q 29Which future Modern Family star played associate Denise Bauer?
Julie Bowen
Bowen joined in season two and left after season three, then won two Emmys as Claire Dunphy.
Q 30After Michael J. Fox's Daniel Post dies, Denise travels to a haunted house to retrieve what?
His head
Post, a terminally ill millionaire, had dated Denise through season two and had his head cryogenically preserved.