Don Cheadle’s 4-Part Legal Masterpiece Deserves Every One Of Its 14 Emmys

Published Oct 1, 2026, 7:00 AM EDT

Memory Ngulube joined Screen Rant in April 2024 as part of the Movies and TV team. Since then, she has written for the Perennials and Streaming team, covering a wide range of topics from new releases to old movies and TV shows. Memory is currently a Classic TV writer. 

Before joining Screen Rant, Memory was a freelance copywriter who specialized in email marketing and social media management. While she enjoyed her job, her true passion was always movies and TV.

When she isn’t writing for Screen Rant, Memory can be found reading, baking (which is one of her passions), or watching her favorite K-drama.

Winning an Emmy is often a career-defining achievement that can cement a series in television history. Over the years, many TV shows have made Emmy history. Game of Thrones took home 59 awards; The West Wing has 26, while Mad Men’s 16 is quite impressive. So, of course, Don Cheadle’s four-season legal drama’s 14 Emmys are a testament to its quality, because not all series have had the honor of scooping up the prestigious award.

In the '90s, Picket Fences proved that legal dramas can have nuance by creating a world where the law was rarely black and white. Despite the show’s critical acclaim and remarkable awards success, the series has gradually faded from the mainstream conversation, leaving one of television's most entertaining legal dramas woefully underappreciated.

Picket Fences had a lot going for it. Though the series could at times tackle bizarre storylines, it's how it handled taboo topics that made it stand out in an era when so many legal dramas were vying for audience attention. While Picket Fences is a masterpiece in several ways, its cast played a huge role in making it one of the best legal dramas of the 1990s.

David E. Kelley’s Picket Fences Is A Forgotten TV Masterpiece

‎David E. Kelley is one of the biggest writers in the television landscape. For years, his name has been associated with prestige legal and medical dramas such as Boston Legal, Chicago Hope, as well as Ally McBeal. Many of Kelley's TV shows, in fact, set the precedent for what truly enjoyable drama should encompass. Recently, Kelley has produced several enjoyable series, including Netflix’s hit legal drama, The Lincoln Lawyer.

Though these aforementioned Kelley series are all excellent in their own right, Picket Fences, with its 27 Emmy Award nominations and 14 wins, is the writer’s crowning glory. At first glance, the legal drama has a simple premise: the series follows Sheriff Jimmy Brock (Tom Skerritt) and his family, along with the town's lawyers, doctors, and residents, as they deal with unusual crimes, legal disputes, and moral dilemmas.

Many have come to associate Kelley with his more well-known shows like Boston Legal, so it's no wonder Picket Fences has faded into the background, though it deserves to be discussed more often. Despite the series debuting more than three decades ago, it foreshadowed the ambitious television to come. Kelley went on to create several other major television dramas, but Picket Fences remains one of the clearest examples of his ability to turn simple premises into something much stranger and more ambitious.

Lawyer John Littleton In Picket Fences Was A Breakout Role For Don Cheadle

While Don Cheadle is now best known as War Machine, Iron Man's smart-mouthed best friend, his acting career began long before that. Of course, the actor has had many notable projects through the years, from Hotel Rwanda to The Guard. However, it's his role as John Littleton in Picket Fences that truly showed he was a generational talent.

Joining the Picket Fences cast in season 2, Cheadle was already demonstrating the qualities that would later make him one of Hollywood's most respected dramatic actors in the David E. Kelley show. His performance in Picket Fences was restrained rather than overly theatrical, allowing Littleton's authority and intelligence to come through naturally. ‎Though Picket Fences is now a forgotten '90s TV show, Cheadle's role in the series is still phenomenal decades later.

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Picket Fences was by no means Cheadle’s first big acting gig. He appeared in The Fresh Prince of Bel Air, The Golden Palace, and Hangin’ with Mr. Cooper, but it is the legal drama that made the industry first take note of him before his role in the 1995 film Devil in a Blue Dress catapulted him to stardom. Today, Cheadle is one of the most respected names in the industry, and his role in Picket Fences proves why.

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  Jimmy Brock

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  Kathy Baker

  Jill Brock

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  Costas Mandylor

  Kenny Lacos

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  Lauren Holly

  Maxine Stewart