Grab yourself a scotch, light up a cigar and relax as we take a look back at Boston Legal on its 20th Anniversary.
It’s been two decades since Boston Legal graced our screens, a time when television courtrooms were either deadly serious or played for melodrama, and along came a series that managed to be both, with a generous side helping of complete absurdity. From its very first episode, Boston Legal demanded attention—whether you liked it or not—thanks to its potent mix of rapid-fire legalese, socio-political satire, and, of course, William Shatner’s unrelenting watchability as the bombastic Denny Crane.
For those who missed out on its five-season run (shame on you), Boston Legal wasn’t your run-of-the-mill legal procedural. If The West Wing was your earnest, politically savvy law professor, Boston Legal was your brilliant but completely unpredictable uncle, showing up at Thanksgiving with a wild grin and a whole suitcase of opinions nobody asked for.
But this wasn’t a two-man show. As much as William Shatner’s Denny Crane and James Spader’s Alan Shore dominated the conversation, the show’s evolving (and somewhat revolving door) cast was essential to the dynamic that made Boston Legal such an unpredictable and delightful watch. It refused to be boxed in. Whether it was through its diverse cast of characters, its daring approach to political and social issues, or its penchant for breaking the fourth wall, this series was as unpredictable as it was groundbreaking.
One of the most striking and pioneering elements of Boston Legal was its portrayal of the friendship between Alan Shore and Denny Crane. In a media landscape that so often pits political opponents as sworn enemies, Boston Legal dared to present two men with starkly different worldviews who not only worked together but shared a deep bond of friendship. Alan, the morally flexible, progressive lawyer, was often the voice of conscience on issues like corporate greed, environmental damage, and social justice. In contrast, Denny Crane, the larger-than-life, right-wing, gun-loving patriarch of the firm, represented a fading conservative America—loud, unapologetic, and sometimes unhinged.
On paper, these two characters should have been at odds, but the show made their friendship central, even as they debated fiercely in the courtroom. It was a reflection of something sorely missing today: the ability to disagree but still respect and care for one another. Their late-night, cigar-and-whiskey balcony chats remain some of the most human and touching moments of the show, blending humour with vulnerability. This dynamic was revolutionary, offering a complex portrayal of political discourse without sacrificing the humanity of either character. Alan and Denny’s friendship wasn’t just a gimmick; it was a testament to the idea that relationships transcend ideologies—something many contemporary shows shy away from exploring.
In a world obsessed with youth and newness, Boston Legal stood out for embracing its ageing stars and turning that into a narrative strength. William Shatner’s portrayal of Denny Crane wasn’t just a nod to his past roles—it was a full-throttle celebration of a character in decline, yet refusing to surrender. His ‘mad cow’ disease became a recurring joke, but the show delicately balanced the humour with real pathos as Denny struggled to remain relevant and competent. Candice Bergen’s Shirley Schmidt was another example of how the show respected age and experience. She was sharp, witty, and effortlessly in control, a character whose maturity wasn’t treated as a weakness but as a weapon.
Unlike most legal dramas that put youth and ambition at the forefront, Boston Legal revelled in the idea that wisdom, built over decades, was just as valuable in navigating the absurd world of Crane, Poole & Schmidt. By allowing its older characters to be flawed, eccentric, and still highly competent, the show broke new ground in television’s portrayal of ageing. It didn’t sideline its veterans for younger stars; instead, it wove their experience into the show’s DNA, turning age into an asset, not a hindrance.
From the outset, Boston Legal established itself as a show unafraid to tackle the big, contentious issues—everything from the death penalty and civil liberties to environmental law and corporate corruption. But rather than falling into the trap of preachiness, the show’s genius was in its characters’ ability to explore these topics from wildly different perspectives. Every character, from Alan Shore to Christian Clemenson’s socially awkward but brilliant Jerry Espenson, brought a different worldview to the table. The show’s true strength was in its eclectic mix of personalities, each one amplifying the discussions on politics, ethics, and justice.
No issue was too big or small for Boston Legal to tackle, and its characters reflected the complexity of the world outside the courtroom. The dynamic cast gave the show room to experiment with tone, switching from laugh-out-loud comedy to moments of genuine, reflective drama without missing a beat. The show never simplified these issues but celebrated the messiness of legal battles and ethical debates by populating its firm with flawed, funny, and often deeply conflicted individuals.
One of the show’s most beloved quirks was its willingness to break the fourth wall. Whether it was Denny Crane reminding everyone of his name as if the audience were characters in the room, or Alan Shore’s knowing glances and asides, Boston Legal revelled in its self-awareness. The show wasn’t just about legal drama—it was about television as a medium and the ridiculousness inherent in both law and entertainment. These moments of meta-humour never detracted from the plot; instead, they heightened the show’s unique charm. By acknowledging its own absurdity, Boston Legal freed itself from the constraints of the traditional legal drama. This self-referential humour made the series feel more alive, as if it were aware it was playing to an audience who understood that life, like law, is often stranger than fiction.
At its core, Boston Legal was a series that took risks—whether in its character portrayals, its handling of hot-button issues, or its refusal to follow formulaic rules. The show blended comedy, politics, drama, and satire in a way that few others have managed, and its ability to engage with real-world issues while remaining wildly entertaining is a testament to its lasting influence. It was a show that celebrated difference—whether through its eclectic ensemble or its embrace of diverse viewpoints—and, in doing so, became a vital commentary on the world outside its fictional courtroom. More than just a legal drama, Boston Legal was a series about what it means to navigate a complex, contradictory world with a little humour and a lot of heart.
Here’s to 20 years of Boston Legal, a show that dared to be different, embraced its eccentricities, and left an indelible mark on television. And of course, here’s to Denny Crane—because in the end, we all remember his name.
