Twenty years after its release, folks still argue about whether De-Lovely is a masterpiece or just a glittering mess of anachronisms. Honestly, it’s a bit of both. But the one thing everyone agrees on? That cast. When Irwin Winkler set out to tell the story of Cole Porter, he didn't just hire actors; he assembled a weirdly perfect collision of Broadway royalty and early-2000s pop stars.
The Anchors: Kevin Kline and Ashley Judd
You’ve got Kevin Kline playing Cole Porter. It’s arguably the role he was born for. He’s got that specific kind of "gentlemanly arrogance" that makes you like him even when he’s being a total nightmare to his wife. Kline actually played the piano himself in the movie. That’s not a stunt; he’s a classically trained pianist. Most of his vocals were recorded live on set too. It gives the film this raw, theatrical energy that you just don't get in modern, over-polished biopics.
Then there’s Ashley Judd as Linda Lee Thomas. She was 20 years younger than Kline in real life, which is kind of ironic since the real Linda was actually eight years older than Cole. But the chemistry works. Judd plays Linda with this heartbreaking "I know exactly what I signed up for" exhaustion. She’s the socialite who stayed with Porter through his endless affairs with men and his ultimate physical decline after that horrific 1937 horse-riding accident.
The Supporting Players
The rest of the core de lovely film cast is filled with heavy hitters:
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- Jonathan Pryce plays Gabe, a sort of spectral director/archangel who guides an aging Cole through the "musical" of his own life.
- Kevin McNally (you know him as Mr. Gibbs from Pirates of the Caribbean) shows up as Gerald Murphy.
- Allan Corduner brings some much-needed wit as Monty Woolley.
- Keith Allen has a brief, somewhat controversial turn as Irving Berlin.
The Pop Star Cameos: A Genius Move or a Distraction?
Basically, the movie is framed as a stage show. Because of that, Winkler decided to have contemporary singers perform Porter’s greatest hits in various "club" settings. It’s jarring at first. You’re watching a 1920s party and suddenly Robbie Williams is there singing the title track.
But then you get Alanis Morissette doing a quirky, theatrical version of "Let's Do It (Let's Fall In Love)" and it somehow makes sense. She even wore a period-accurate dress and had a little speaking part.
Sheryl Crow shows up for "Begin the Beguine," and Elvis Costello delivers a grimy, energetic "Let's Misbehave." These aren't just background tracks; they are full-blown performances that ground Porter’s music in the "now." The standout, though, has to be Natalie Cole singing "Ev'ry Time We Say Goodbye" near the end. It’s gut-wrenching.
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What Most People Get Wrong About the Casting
Some critics at the time felt the de lovely film cast was too "theatrical." They wanted a gritty, realistic drama. But Cole Porter didn't live a gritty, realistic life. He lived in a world of rhyme schemes and champagne.
Also, a lot of viewers think the singers were just there for the soundtrack sales. While the soundtrack did well, many of those artists—like Diana Krall and John Barrowman—were chosen because they actually understood the Great American Songbook. Barrowman, in particular, is fantastic as "Jack," performing a duet of "Night and Day" with Kline that feels like a genuine Broadway moment.
Real Details You Might Have Missed
- Lara Fabian and Mario Frangoulis perform a show-stopping version of "So In Love" that usually makes people stop and Google who they are.
- Caroline O'Connor plays the legendary Ethel Merman. It's a tiny role, but she nails the brassy "Merman" belt.
- Vivian Green delivers a soulful, jazzy "Love for Sale" that highlights the darker undertones of Porter's lyrics.
Why It Works Today
The film doesn't shy away from Porter's sexuality, which was a big deal for a mid-budget MGM movie in 2004. It portrays a "Lavender Marriage" with a lot of nuance. It shows that Cole and Linda loved each other deeply, even if their bedroom life was... complicated.
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The casting of Kline and Judd is what makes that pill easy to swallow. You believe they are a team. You believe they are the only two people who truly understand the "Cole Porter" brand.
If you're looking to revisit this one, don't just watch it for the history. It’s not a history lesson. It’s a fever dream of a man looking back at his greatest hits and his greatest regrets.
Next Steps for the Fan:
- Listen to the original recordings: After watching Kline, go back and listen to Cole Porter’s actual voice on "You're the Top." It’s thin and reedy, making Kline's performance seem even more impressive.
- Check out the 1946 version: Watch Night and Day starring Cary Grant. It’s the "sanitized" version of Porter’s life where his sexuality is completely erased. It makes the 2004 film look like a revolutionary document.
- Track down the soundtrack: Some of the arrangements by Stephen Endelman are genuinely better than the Broadway originals.