If you were scrolling through television channels in 1999, you might have stumbled upon a person in a shimmering French naval jacket, high heels, and a face full of makeup talking about the strategic use of flags. It was weird. It was brilliant. It was Eddie Izzard Dressed to Kill, a stand-up special that basically redefined what a solo performance could look like.
Most comedy ages like milk. What was "edgy" in the late nineties usually feels cringey or problematic by today's standards. But this set? It’s different. Izzard—who now uses she/her pronouns and often goes by Suzy, though this special captures a specific "executive transvestite" era—managed to weave together world history, religion, and the absurdity of jam in a way that feels oddly timeless.
The Night at the San Francisco Shoreline
Recorded at the we-wish-we-were-there Shoreline Amphitheatre (well, technically the smaller, more intimate venue within the city), Dressed to Kill wasn't just another HBO special. It was a victory lap. Izzard had already conquered London with Definite Article and Glorious, but America is a different beast. To win over a US audience, she didn't simplify the material. She just leaned harder into the surrealism.
The stage was simple. One stool. One microphone. One performer who looked like a glam-rock pirate.
The energy in that room was electric because the audience wasn't just watching jokes; they were watching a masterclass in "stream of consciousness" that actually had a backbone. You've got to realize that most comics back then were doing "setup-punchline, setup-punchline." Izzard was doing "Viking history-squirrels-the Pope's secret life." It felt dangerous and smart at the same time.
What Made Eddie Izzard Dressed to Kill a Cultural Reset?
People often forget how much of a gamble this was. At the time, Izzard identified as a transvestite—her words—and her presence on stage in "women’s clothing" wasn't a gimmick. It was just who she was. She famously said she didn't wear "drag," she just wore clothes. That distinction is huge. It removed the "performance" of gender and replaced it with a raw, intellectual honesty that let the comedy breathe.
The History Lessons You Actually Remembered
Honestly, I learned more about the British Empire from this special than I did in three years of secondary school. The "Cake or Death" bit is the obvious standout. It’s the quintessential Izzard moment. The idea of the Church of England as a polite, terrifying entity offering refreshments instead of eternal damnation is genius.
"You! Cake or death?"
"Uh, cake please."
"Very well! Give him cake!"
It sounds simple, but it’s a critique of imperialism, bureaucracy, and the banal nature of evil, all wrapped up in a bit about baked goods.
Then you have the segment on Stonehenge. Most people look at those rocks and think "druids" or "mystery." Izzard looks at them and sees a massive logistical nightmare involving rolling stones on logs while someone screams, "I’ve lost my finger!" It’s that pivot from the grand to the granular that makes her writing—if you can call her improvised ramblings writing—so potent.
The Language Barrier That Wasn't
One of the coolest things about Eddie Izzard Dressed to Kill is how she handles the "two countries divided by a common language" trope. She spends a good chunk of time explaining Britishisms to the San Francisco crowd, but she does it without being condescending.
She talks about "herbs" with the 'H' and how Americans say "ERB" because, apparently, "there's no H in it." It’s a silly observation that taps into a deeper truth about cultural identity. She was building a bridge. By the time she gets to the bit about the French being "a bit... French," she has the audience in the palm of her hand.
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The Technical Brilliance of the "Mime"
Izzard is a physical comedian, though she doesn't get enough credit for it. Think about the way she portrays a cat trying to use a drilling machine. Or the way she mimes a squirrel hiding a nut. She doesn't need props. Her hands, her posture, and those subtle facial shifts do all the work.
In Dressed to Kill, the physical bits act as a palate cleanser. When the history gets too dense—moving from the Roman Empire to the fall of Constantinople—she’ll drop in a bit of physical absurdity to reset the room. It’s a pacing trick that many modern comics try to emulate but rarely master.
Why the "Executive Transvestite" Label Mattered
In 1999, the vocabulary for gender non-conformity was limited. Izzard used the term "executive transvestite" to describe her look. It was a way of saying, "I am queer, but I am also powerful and professional."
Looking back, it was a radical act of visibility. She wasn't playing a character. She wasn't the butt of the joke. She was the smartest person in the room, wearing eyeliner and heels, explaining why the Spanish Inquisition was a bit of a failure because "no one expects the Spanish Inquisition!" (Wait, that’s Python—but Izzard’s take on the Catholic Church’s "surprise" tactics was equally sharp).
She showed a generation of people that you could be "different" and still be universally funny. You didn't have to be a caricature.
The Legacy of the Flag
"No flag, no country! You can't have one!"
This bit about the British Empire claiming lands simply because they had a bit of cloth on a stick is probably one of the most cited pieces of stand-up in history. It’s a perfect observation. It strips away the "glory" of colonialism and reveals it for what it was: a land grab based on arbitrary rules.
Scientists, historians, and even politicians have quoted the "Flag" bit. It’s more than a joke; it’s a philosophical argument. When you watch Eddie Izzard Dressed to Kill today, that segment feels even more relevant as the world continues to grapple with the fallout of those "flags."
What People Get Wrong About the Improvisation
There’s a common misconception that Izzard just makes it all up on the spot. While she is a queen of the "tangent," the structure of Dressed to Kill is incredibly tight. If you watch different recordings from that same tour, the beats are there. The "Le Singe est sur la branche" bit? That’s a calculated payoff.
The brilliance lies in making the rehearsed feel spontaneous. She’ll pause, look at her fingernails, mutter "um" or "so, yeah," and make you feel like she just thought of a brilliant connection between Pol Pot and a dinner party. That’s the "human" element that AI or lesser comics can’t replicate. It’s the sound of a brain working in real-time.
How to Re-watch Dressed to Kill in 2026
If you haven't seen it in a while, or if you're a younger fan who only knows Suzy Izzard from her recent political activism or marathon running, you need to go back to this source material.
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It’s currently available on various streaming platforms, and honestly, the low-res 1999 video quality adds to the charm. It feels like a transmission from a different world—a world that was just beginning to understand that comedy could be surreal, educational, and gender-fluid all at once.
Actionable Insights for Comedy Nerds and History Buffs
- Study the "Rule of Three" subversion: Izzard often goes to a "Rule of Five" or "Rule of Seven," pushing a joke way past its breaking point until it becomes funny again.
- Observe the "CallBack": Pay attention to how she brings back the "squirrels with guns" or the "jam" references. It’s a masterclass in knitting a show together.
- Look for the Humanity: Beyond the jokes, notice how she treats her subjects. She mocks institutions, not people (well, except for maybe the incredibly stupid ones).
- Analyze the Transition: Watch how she moves from the literal (her shoes) to the metaphorical (European history). It’s a seamless shift that keeps the audience engaged without them realizing they’re being taught something.
The reality is that Eddie Izzard Dressed to Kill remains the gold standard for intellectual stand-up. It proved that you don't have to talk down to an audience. You can talk about the Enlightenment, the French Revolution, and James Bond's internal monologue, and if you're funny enough, they'll follow you anywhere. Even into the darkness of a "Cake or Death" scenario.
If you’re looking to dive deeper, compare this special with her later work like Force Majeure. You’ll see the evolution of a performer who went from explaining her identity to the world to simply living it, all while never losing that signature, chaotic, brilliant wit.
To truly appreciate the craft, watch the special without distractions. Turn off your phone. Let the tangents take you. You'll find that the "random" thoughts are actually a very deliberate map of a brilliant mind. And maybe, just maybe, you'll never look at a flag the same way again.
Next Steps for Fans:
- Track down the "Glorious" special to see the precursor to this style; it’s the "Empire Strikes Back" to Dressed to Kill's "A New Hope."
- Read Izzard's autobiography, "Believe Me," for the actual backstory on the night this was filmed and the mental state she was in during the San Francisco run.
- Check out her recent "Hamlet" solo performance to see how that 1999 energy has evolved into Shakespearean acting.
The special isn't just a relic of the nineties; it’s a blueprint for anyone who wants to be authentically themselves while making the world laugh at its own absurdity.