Join our Waitlist for Expert Advice!

Steve Ballmer's Most Awkwardly Hilarious Moments As he gets ready to buy the LA Clippers basketball team, a look back at the former Microsoft CEO's most unusual public antics.

By Jason Fell

Steve Ballmer is a former tech executive who's about to buy a basketball team. He's also an awkwardly funny dude.

Yesterday, news broke that Ballmer -- the former longtime Microsoft CEO -- had agreed to buy the Los Angeles Clippers basketball team for $2 billion. From the board room to the basketball court. Why not, right?

Ballmer, as you may recall, stepped down as Microsoft's chief executive in February after serving in that role since 2000. During that time, Microsoft had some hits (Windows, Office, XBox) and some big misses (Vista, Windows 8, anything mobile). Under Ballmer, Microsoft's annual revenue grew from $25 billion to $70 billion, and net income increased 215 percent to $23 billion.

Related: Steve Ballmer to Retire as Microsoft CEO

If you paid attention to Ballmer and Microsoft during that time then you've likely also been witness to one or two -- or several -- of his painfully awkward public moments. He yells. A lot. He sweats. He jumps around. He teams up with Microsoft co-founder Bill Gates for really corny spoof videos.

The list goes on. And on.

Because it's Friday -- and, why not? -- here are just a few examples of Ballmer at his most awkward, arguably at his best. Enjoy.

Ballmer plays Dr. Evil in this Austin Powers spoof with Gates. (Yes, Clippers fans, this is your new owner.)

Sometimes he gets excited. Like, really excited.

He loves developers. (Can you tell?) He also sweats. A lot.


And, finally, Ballmer and Gates do Night at the Roxbury. Seriously.

Related: Why All the Hate for Microsoft CEO Steve Ballmer?

Jason Fell

Entrepreneur Staff

VP, Native Content

Jason Fell is the VP of Native Content, managing the Entrepreneur Partner Studio, which creates dynamic and compelling content for our partners. He previously served as Entrepreneur.com's managing editor and as the technology editor prior to that.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Business News

Doctors Are Using AI to Transcribe Conversations With Patients. But Researchers Say the Tool Is Hallucinating 'Entire' Sentences.

The tool malfunctioned 312 times in one study, leading to concerns about bias and misdiagnoses.

Operations & Logistics

The Port Strike Ended — Now What? Here's How Small Businesses Can Prepare for Future Disruptions.

The shutdown lasted only three days, and the ILA and the U.S. Maritime Alliance extended their contracts until January 15, 2025 — but if they can't reach an agreement in the new year, the dockworkers could go on strike again.

Business News

You Have One Month Left to Buy a House, According to Barbara Corcoran. Here's Why.

"If you are planning on waiting a year and seeing where interest rates go, you are out of your mind," Corcoran said.

Business News

A Wells Fargo Worker Was Discovered 4 Days After Dying at Her Desk. Her Cause of Death Was Just Revealed.

Medical examiners have released the cause of death of Denise Prudhomme, who was found dead at her desk in Wells Fargo's Tempe, Ariz. office.

Business News

Meta Fires Employee Making $400,000 Per Year Over a $25 Meal Voucher Issue

Other staff members were fired for the same reason, per a new report.