Microsoft’s Most Memorable Commercials

Microsoft’s journey in advertising mirrors its own corporate evolution: from the brash, monopolistic tech giant of the 90s to the more empathetic, cloud-focused, and accessibility-driven behemoth of today. Its most memorable commercials are not always its most polished, but they are pivotal moments that defined—or redefined—the company's relationship with consumers, often in response to competitive and cultural pressures. This article explores the commercials that left an indelible mark, charting Microsoft's path from selling operating systems to selling hope, innovation, and inclusivity.

The Era of Dominance: The 1990s

1. Windows 95 Launch: "Start Me Up" (1995)

The Campaign: To launch Windows 95—an operating system featuring the revolutionary Start button—Microsoft licensed The Rolling Stones' iconic song "Start Me Up" for a reported $8-14 million. The ads showed everyday people (and a surprisingly excited Jay Leno) gleefully clicking the Start button to a rock & roll soundtrack.
Why It's Memorable: It was a cultural event, not a product demo. The use of a legendary rock anthem signaled that software was now mainstream, exciting, and central to pop culture. It cemented Windows as the platform for the future.
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2. "Where Do You Want to Go Today?" (1994)

The Slogan: This aspirational, open-ended tagline underpinned a series of cinematic ads showing diverse people using technology in uplifting ways—a teacher with students, a doctor consulting remotely.
Why It's Memorable: It marked Microsoft's first major attempt at emotional, brand-level advertising. It shifted focus from bits and bytes to human potential, positioning Microsoft as an enabler of dreams during the dot-com boom. The slogan became synonymous with 90s tech optimism.

The Defensive Era: Responding to Apple & Perception (2000-2010)

This period was defined by Apple's devastatingly effective "Mac vs. PC" campaign. Microsoft's ads were often reactive, trying to rebuild a battered image.

3. The "I'm a PC" Response Campaign (2008)

The Campaign: Directly countering Apple's personification of a PC as a dorky loser (John Hodgman), Microsoft launched this spot featuring a diverse cast—from celebrities like Eva Longoria and Deepak Chopra to everyday people, scientists, and a young child—all stating proudly, "I'm a PC." It culminated with Microsoft's own "dorky" star, Bill Gates, appearing.
Why It's Memorable: It was a necessary, well-executed act of brand rehabilitation. It reframed "PC" as a badge of pride for a vast, global community of achievers, reclaiming the narrative from Apple. It was Microsoft fighting back with scale and inclusivity.
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4. Windows 7 Launch: "I'm a PC, and Windows 7 was my idea" (2009)

The Campaign: This follow-up continued the "I'm a PC" theme but focused on the collaborative development of Windows 7, suggesting it was built with feedback from millions of users.
Why It's Memorable: It cleverly positioned a product launch as a democratic triumph, contrasting with Apple's top-down, "we-know-best" aura. It was a strategic move to portray Microsoft as humble and customer-centric.

The Aspirational & Product-Centric Renaissance (2010-2015)

With the launch of Windows 8, Surface, and new cloud tools, Microsoft's advertising became more product-forward and visually stunning.

5. Microsoft Surface "Click" (2012)

The Campaign: A mesmerizing ad showing the magnetic "click" of the Type Cover to the Surface tablet, set to a percussive soundtrack. It was sleek, silent, and focused on a single, satisfying hardware differentiator.
Why It's Memorable: It announced Microsoft as a serious hardware designer. The ad was a stark departure from software-centric messaging and was praised for its minimalist elegance. It aimed to generate desire through tactile sensation.
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6. "Child of the 90s" Internet Explorer Ad (2012)

The Campaign: A surprisingly nostalgic and self-deprecating ad for Internet Explorer 9. It acknowledged the browser's poor reputation ("You grew up. So did we.") with a montage of 90s pop culture references (Tamagotchis, Bill Clinton, Clueless).
Why It's Memorable: It was a masterstroke of brand humility. By admitting past flaws and aligning with shared nostalgia, it attempted to disarm critics and invite a second look. It showed Microsoft could laugh at itself.
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7. "Empowering" with Braylon O'Neill (2014)

The Campaign: A profoundly moving ad featuring Braylon O'Neill, a young boy born without fully formed limbs, using a Surface Pro 3 with a stylus to draw, play, and express his creativity. The ad focused entirely on his story, with the product as a seamless enabler.
Why It's Memorable: It was arguably Microsoft's most powerful mission-driven ad. It moved beyond selling specs to showcasing technology's transformative potential for human dignity and ability. It aligned perfectly with CEO Satya Nadella's emerging focus on "empowering every person."
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The Nadella Era: Empathy, Cloud, and AI (2015-Present)

Under Satya Nadella, Microsoft's advertising has emphasized empathy, accessibility, and its role as a platform for other people's success.

8. "Meet the Superhumans" for Xbox Adaptive Controller (2018)

The Campaign: A gripping, Paralympics-style ad showcasing gamers with disabilities using the Xbox Adaptive Controller. Set to a remix of Sammy Davis Jr.'s "Yes I Can," it was raw, empowering, and celebratory.
Why It's Memorable: It positioned a niche gaming accessory as a symbol of radical inclusive design. It won numerous awards and demonstrated Microsoft's commitment to accessibility as a core innovation driver, not just charity.
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9. "Be the One" (2018) & "What Will You Do?" (2021)

The Campaigns: These LinkedIn ads (Microsoft acquired LinkedIn in 2016) focused on career empowerment. "Be the One" showed pivotal moments in job searches, while "What Will You Do?" was an anthem for the post-pandemic "Great Resignation," encouraging people to seek better work.
Why It's Memorable: They successfully marketed a professional network with deep emotion. They showcased Microsoft's growing portfolio of "cloud and productivity" tools by highlighting human outcomes—finding purpose, landing a dream job.

10. "Seeing AI" Demo with Steve Gleason (2023)

The Campaign: A poignant demonstration featuring former NFL player Steve Gleason, who has ALS, using the Seeing AI app. The app, powered by Azure AI, narrates the world for him, describing his son's facial expressions as they watch a football game together.
Why It's Memorable: It is the ultimate synthesis of Microsoft's modern pillars: AI, cloud computing, and accessibility, wrapped in a deeply human story. It makes complex AI tangible and emotional, showing it as a bridge to human connection rather than a scary abstraction.
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Table: The Evolution of Microsoft's Messaging

EraIconic Campaign / SloganCore MessageCultural & Competitive Context

1990s Dominance	"Start Me Up" (Win 95)	Software is exciting, mainstream, essential.	Peak of PC dominance; tech enters pop culture.
2000s Defense	"I'm a PC" (2008)	Inclusivity & Pride in the PC ecosystem.	Direct response to Apple's "Get a Mac" attacks.
2010s Aspiration	Surface "Click" / Braylon O'Neill	Design excellence & Technology as an empowerment tool.	Launching hardware; rebuilding brand image with empathy.
2020s Empathy & AI	"Meet the Superhumans" / "Seeing AI"	Inclusive Design & AI for human good.	Nadella's "Empowerment" ethos; focus on accessibility & cloud/AI.

Expert Analysis: The Shift from Swagger to Soul

"Microsoft's advertising journey is a classic case of a market leader learning to lead with vulnerability," observes a brand strategist. "In the 'Start Me Up' days, it was pure, confident swagger. The 'I'm a PC' era was defensive solidarity. But the true turnaround began with ads like Braylon O'Neill's and the Adaptive Controller—ads that sold a mission, not just a product. Under Nadella, Microsoft found a higher-purpose story: technology as a tool to uplift every person, which is a far more resilient and likeable brand platform than mere market dominance."

The most memorable Microsoft commercials now succeed by humanizing technology. They showcase the user, not the UI. They tell stories where Microsoft's products are the quiet, capable sidekicks to human achievement, struggle, and connection.

Conclusion: From Operating Systems to Operating with Purpose

Microsoft's most memorable commercials chart a path from selling the utility of technology to selling its humanity. The arc moves from the explosive excitement of a Start button to the quiet miracle of an AI app helping a father see his son's smile.

This evolution reflects a broader truth in tech marketing: as products become more complex and integrated, the most powerful stories are not about what the technology does, but what it allows us to do. Microsoft's legacy in advertising will likely be defined not by the jingle that launched Windows 95, but by the demonstrations that prove technology, at its best, is a bridge—to opportunity, to creativity, and to each other.

YouTube Playlist of Memorable Microsoft Commercials:

Windows 95 "Start Me Up":

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"I'm a PC" Campaign (2008):

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Microsoft Surface "Click" (2012):

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Internet Explorer "Child of the 90s" (2012):

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"Empowering" – Braylon O'Neill (2014):

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Xbox Adaptive Controller "Meet the Superhumans" (2018):