From the Gmail Man, who peeks into people's private mail, to the VMware salesman stuck in the '70s, Microsoft's marketing campaigns have become quite pointed in the past year.
This week, the company will launch another such campaign: "Smoked by Windows Phone," a series of online ads challenging those who use iPhones, Android phones or other mobile devices to beat the speed of a Windows Phone in doing a browser search, sharing with their social network or shooting and posting a photo.
The 12 different digital ads featuring the challenge will run on tech sites as well as the Windows Phone Facebook page through the beginning of April.
Also on the Facebook page will be video footage from the original "Smoked by Windows Phone" challenge, which took place at the Consumer Electronics Show in January. There, at the Microsoft booth, CES attendees participated in speed challenges, winning $100 if their smartphone beat the Windows Phone.
The final tally for Windows Phone at the CES challenge: 30 wins, three losses, one tie.
That original challenge and the online campaign launching this week, are examples of a funnier, sharper, more direct and aggressive - and sometimes snarkier - approach to marketing for the software giant generally known for more earnest, wholesome ads.
It could even be seen as the scrappy move of an underdog - which Microsoft is, in search and mobile, if such a thing could be said of a company that logged nearly $70 billion in revenue and $23 billion in profit in the past fiscal year.
"Over the last year, one of the things that we've actually done is say: 'We're not going to sit on the sidelines when our competitors do things that we disagree with,' " said Frank Shaw, corporate vice president of corporate communications at Microsoft. "We're going to make sure that we tell our story, with all the assets that we have."
How the approach has played out:
-Last summer at an internal conference, Microsoft showed a Gmail Man spoof video, in which a mailman dubbed Gmail Man looks into your private mail ("he peeks at every subject in un-real time").
It coincided with the launch of several ads in major newspapers that week in which Microsoft skewered Google's privacy-policy changes while touting Microsoft products and services.
Google fired back in a company blog post, saying that "a number of myths are being spread about Google's approach to privacy."
A Google spokesperson could not immediately be reached for comment.
-In August, Microsoft released a video spoofing competitor VMware, saying the Palo Alto, Calif., company's emphasis on virtualization technology was stuck in the past.
-Also in August, Microsoft went after Salesforce.com and VMware in a series of ads and incentive offers for companies that switch from those companies to Microsoft's Dynamics CRM Online.
-And Shaw has not been shy about exchanging zingers on Twitter. After Google characterized Microsoft's patent-licensing program as extortion, Shaw tweeted that he had one word for Google: "Waaaah."
Shaw disagrees with the characterization of the approach as sometimes "snarky." It's all about communicating with audiences directly, he said, which these days include online ads, blog posts, social media, videos and infographics, as well as print and TV ads.
The humor and attitude, he said, is intended to break through "with the audiences we care about. ... People appreciate a real human voice to the story."
Not to say Microsoft doesn't still produce the earnest family-oriented ads people usually associate with the company.
There's the "It's a great time to be a family" ads geared at showing how Microsoft products work together to help families spend more time together.
And there's the stirring "Kinect Effect" ad, in which the company shows examples of real-life uses of the Kinect motion and voice sensor (from the operating room to a musician's practice room) that Microsoft never envisioned.
"That's absolutely the Microsoft voice. That's where we're spending our big dollars," Shaw said.
But Microsoft has come to realize it has a scrappier, jabbier voice, too, he said.
That's quite a change for a company that's battled years of perceptions that it's stodgy and dull - best distilled, perhaps, in a series of "I'm a Mac" ads from rival Apple.
Shaw won't divulge numbers but said the approach is garnering good results, especially in terms of return on investment.
"I don't know that there was any one 'aha!' moment that said we're (going to do this)," Shaw said. "There have been times in the past when we've been quiet even when we've had something to say. Today we feel: We have tough competition. ... If we have a story to tell, if we have something to say, we should say it. "
Explore further: Ford recalls 432K cars because of software problem