The outrageous, surprising, and prescient legacy of Boston Legal

Ten years after its premiere, the legal drama stands out for its unwavering commitment to pushing boundaries

Boston Legal
(Image credit: (AP Photo/ABC, Dean Hendler))

Ten years ago this month, the lawyers at Crane, Poole, and Schmidt arrived on television. Juxtaposing progressive ideas with an old-world style that included plenty of cigars and whiskey, Boston Legal breathed new life into one of television's most well-worn tropes: the legal thriller.

But for all its courtroom trappings, Boston Legal wasn't really about upholding the law — it was about pushing the law past its limits. Every week, the show's lawyers would argue cases that stretched beyond the boundaries of the law and delved into the boundaries of society. Sometimes those boundaries would push right back. But other times, the show's "stretches" were just the torchbearers for new cultural norms.

The firm's very first "outrageous" case is now reality. In Boston Legal's premiere, Alan Shore (James Spader) argues on behalf of a talented young singer refused the part of Little Orphan Annie because she was black. The case is framed as the type that Boston Legal would later describe as "typically preposterous" and "unwinnable," and extreme enough that Shore needed a "magic rabbit" to win: Reverend Al Sharpton fervently monologuing about progress always being a day away. Alan won the case in the fictional world a decade ago, and — in a case of life imitating art — Beasts of the Southern Wild's Quvenzhane Wallis will play Annie in a film adaptation this winter.

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But Boston Legal was far more than a moral compass for the future. The show relished the immorality of the characters in its core relationship: the idealistic, inappropriate Alan Shore, and the absurdly conservative Denny Crane (William Shatner). "You ooze that certain something that subliminally champions misogyny," a fellow lawyer tells Shore when he joins the firm. Together, Crane and Shore exacerbate each other's worst impulses — especially with women. As the show's reliable anchors, Alan and Denny seem to be quintessential men: one conservative, one liberal, but both in love with women, sex, whiskey, and cigars. They also stand as the firm's kingpins of sexual harassment.

But creator David E. Kelley's treatment of the theme in Boston Legal says much about the show's approach. His sexist protagonists are at the heart of the show, so they can't be fired, but a sudden change of heart would be disingenuous and unbelievable. Instead, depicting the protagonists' sexism gave Boston Legal the opportunity to explore it: the ways it manifested itself, the many ways women would react, and, at times, the latent motivations behind it.

Boston Legal's sexist trappings seemed, at first, to fall within its era's norms for both society and television. The show's men were older, smarmier, and a touch out of shape; the women around them were invariably young and gorgeous. But the show didn't stop there. In addition to flirtations and flings with the women you'd expect, the show began to broaden the types of women it would cast in romantic narratives — particularly with Denny Crane's on-again, off-again flirtation with fellow lawyer and little person Bethany (Meredith Eaton). Denny and Alan's tastes had little, if any, limits — and ultimately, no woman could match their shared obsession with the almost 60-year-old partner Shirley Schmidt (Candice Bergen).

Schmidt was the catch — the woman both men desperately wanted above all others, and who remained eternally out of reach. It wasn't because she was botoxed, lifted, and bursting with Sophia Loren-levels of timeless sexuality. Shirley Schmidt was, quite simply, a paragon of womanhood.

Schmidt's arrival in the middle of Boston Legal's first season brought an added sense of openness to both the cast and storylines. As the show's younger actresses departed, they were replaced with the likes of Schmidt, Betty White, and stories about people struggling with boredom and age. Christian Clemenson soon joined the mix as Shore's second-closest friend, Jerry Espenson, a lawyer with Asperger's whose actions ranged from random outbursts of violence to an atypical romance with an objectophile. Gary Anthony Williams later joined the team as the cross-dressing Clarence, and gradually evolved into a thoughtful, aspiring lawyer who helped bridge the divide between the partners and the new associates.

As the series went on, the lawyers at Crane, Poole, and Schmidt would break the fourth wall to complain about the restrictions on their storylines and fight to stay in production. At one time, Boston Legal had one of the most diverse sets of secondary characters in television; when its pared-down final season did away with most of them, Alan Shore lamented "the systemic racism of the firm." No one — not the characters, backers, or the show itself — was off-limits.

Boston Legal was never satisfied with being one thing. It would drum up heartwarming nostalgia by resurrecting old clips of Shatner in Defenders to portray a young Denny Crane, then reel back to have Denny Crane scheme for the love of Raquel Welch. Alan Shore would help out an ex who once tried to kill him, then dress up as Batman and partake in vigilante justice for kicks. The show wasn't interested in defending itself, or a character, in some rigid declaration of purpose; within its stories, and as a TV show as a whole, it was interested in defending and depicting the virtue of change.

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Monika Bartyzel

Monika Bartyzel is a freelance writer and creator of Girls on Film, a weekly look at femme-centric film news and concerns, now appearing at Her work has been published on sites including The Atlantic,, Moviefone, Collider, and the now-defunct Cinematical, where she was a lead writer and assignment editor.