Conan O’Brien Dresses as Steve Jobs?
Yes, Conan O’Brien has dressed as Steve Jobs multiple times on his shows, most notably in a recurring sketch on Conan (TBS) called “Celebrity Surpriseâ€� where he impersonated Jobs to prank unsuspecting fans. The bit combined a fake prize giveaway with O’Brien’s exaggerated take on Jobs’s iconic black turtleneck, jeans, and New Balance sneakers, and it became one of his most popular recurring segments.
Background: The “Celebrity Surprise� Sketch
The “Celebrity Surpriseâ€� sketch first appeared on Conan in the early 2010s. The premise was simple: a fan is told they’ve won a prize, and while they wait, they’re greeted by a celebrity—except the celebrity is actually Conan in a cheap costume. The Steve Jobs version was a standout because O’Brien’s portrayal was less about physical resemblance and more about a comedic caricature: he wore a black long-sleeve shirt (often a mock turtleneck), jeans, and sneakers, and spoke in a slow, deliberate, faux-CEO cadence. The humor came from the absurdity of the situation—fans would often be confused or starstruck before realizing it was Conan.
Other Times Conan Dressed as Jobs
Beyond “Celebrity Surprise,â€� O’Brien donned the Jobs look for other segments. On Late Night with Conan O’Brien (NBC) in the 2000s, he occasionally used a Jobs-style outfit for bits about Apple product launches, parodying the hype around new iPhones and iPods. He also reprised the character during his 2010–2011 “Legally Prohibited from Being Funny on Televisionâ€� comedy tour, where he appeared in a video mocking the tech industry. In each instance, the costume was intentionally low-budget—a nod to the fact that O’Brien’s tall, lanky frame and red hair made him an unlikely Jobs lookalike.
Why This Particular Impression Works
Steve Jobs’s public image was so consistent—black turtleneck, Levi’s 501 jeans, New Balance 991 sneakers—that even a minimal costume reads as “Jobsâ€� to most audiences. O’Brien leaned into that by adding his own comedic tics: a slow, deliberate walk, a deadpan stare, and lines like “I have a visionâ€� delivered with faux-solemnity. The contrast between Jobs’s real-world reputation as a visionary and O’Brien’s self-deprecating humor created a rich source of parody. It also helped that Jobs rarely appeared in public in anything else, so the outfit was instantly recognizable.
How the Sketch Was Structured
The typical “Celebrity Surprise� segment followed a formula:
- The host introduces a fan who has won a “mystery prize� (often a cheap item like a toaster).
- The fan is led to a room where Conan, in costume, is waiting.
- Conan delivers a few lines as the celebrity, trying to keep a straight face.
- The fan eventually realizes it’s Conan, leading to laughter and a chat.
For the Jobs version, Conan would often enter with a prop—like a cardboard Apple box—and speak about “revolutionaryâ€� products that were actually mundane items (e.g., a “wirelessâ€� sandwich). The sketch relied on the fan’s genuine reaction, which ranged from confusion to delight.
Reception and Cultural Impact
The sketch was well-received by fans and critics, with many praising O’Brien’s willingness to mock himself and the tech industry. It also became a YouTube favorite, with clips racking up millions of views. The impersonation was so popular that it was referenced in later media, including a 2015 episode of The Simpsons (where O’Brien guest-starred as himself in a similar bit). While not as iconic as his “In the Year 2000â€� or “If They Matedâ€� sketches, it remains a memorable part of his late-night legacy.
Common Misconceptions
One misconception is that Conan’s Jobs impression was a direct mockery of Jobs’s personality. In reality, O’Brien has said in interviews that he admired Jobs and was poking fun at the tech industry’s hype culture, not the man himself. Another misconception is that the sketch was a one-off; it actually appeared several times, with different fans and variations. Some also confuse it with other celebrity impersonations Conan did (like his Donald Trump or Tom Cruise), but the Jobs version is distinct in its simplicity.
Frequently Asked Questions
Did Conan O’Brien ever meet Steve Jobs?
There is no public record of O’Brien meeting Jobs. The sketch was purely a comedy bit, and O’Brien has never claimed a personal interaction. Jobs was notoriously private, so it’s unlikely they crossed paths.
What did Conan actually wear for the Jobs costume?
He wore a black long-sleeve shirt (often a mock turtleneck), blue jeans, and white or gray sneakers. It was a generic version of Jobs’s uniform, not an exact replica. He also wore glasses in some versions, though Jobs famously did not wear glasses in public.
Is the sketch still available to watch?
Yes, clips of “Celebrity Surprise� featuring the Steve Jobs bit are available on YouTube and other video platforms. The official Conan channel has posted several full segments. However, some clips may be region-locked or removed over time.
Did Conan do this on other shows besides TBS?
Yes, he used the Jobs outfit on Late Night and The Tonight Show for brief bits, but the “Celebrity Surprise� version was exclusive to his TBS show. The earlier appearances were usually shorter and part of larger comedy segments.
Why did the sketch end?
The show was canceled in 2021, so the sketch ended with it. O’Brien has moved on to other projects, including a podcast and travel specials, but he hasn’t reprised the Jobs character since.
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