David Bloom is a contributor to Deadline.

Microsoft’s announcement this morning that Steve Ballmer, the oldest of the old guard at what was once the biggest of the big tech companies, is leaving as CEO should be a major deal in Hollywood as well as Silicon Valley. After all, Ballmer and the tech giant he’s helped run for more than three decades have spent billions of dollars on countless entertainment-related initiatives trying to take their tech success to Tinseltown, including the latest big hire of former CBS network chief Nancy Tellem as president of Microsoft’s entertainment and digital media division. But will Hollywood notice Ballmer’s departure? Not really. He doesn’t even do the big CES keynote address anymore. And Hollywood’s likely indifference says a lot about Ballmer, Microsoft and the challenges the entire tech industry continues to have in decrypting Hollywood (and to be fair, vice versa).

Related: Microsoft CEO Steve Ballmer To Retire Within Next Year

At the May unveiling of the Xbox One, Tellem got on stage to say her unit is producing video programming for the console across every genre. She intimated that the studio’s programming would move far beyond traditional television, to take full advantage of the connectivity, motion-detection, emotion-detection and other interactive capabilities of the Xbox One. Less clear is whether that interactive programming will find an audience, especially given Xbox One’s high price, poor E3 showing and competition from a new Sony device and lots of far cheaper and more mobile alternatives. Audience sizes, especially in the first couple of years of the new console, will almost certainly be uncomfortably small for yet another expensive entertainment venture.

To head off some of that, as Deadline’s Nikki Finke and David Lieberman wrote, Ballmer recently joined Tellem on a series of meetings with Hollywood big-shots. The June trip was designed to both test support for their programming initiatives and build more interest among talent, dealmakers and producers. What hasn’t surfaced is whether those conversations have turned into anything substantive.

Related: Nancy Tellem Talks Xbox Entertainment Studios, Finally

Microsoft is a mature company, and its core products are under assault from many far-cheaper and more web-savvy options. The Xbox division has been a big success ($8.9 billion in 2012 revenues), but its head, Don Mattrick, left a month after that bad E3 to take over as CEO of Zynga. That Mattrick chose to take over a badly struggling game-software company rather than stick around six months to launch the next Xbox says a lot.

Perhaps the most telling story about Microsoft’s flailing about with Hollywood has been its challenges getting a movie or TV show, really anything, made from its iconic Halo video game franchise, which single-handedly made the original Xbox game console viable against industry powers Sony and Nintendo. Halo has a rich sci-fi backstory, compelling lead character and its own movie-worthy cinematics. A dozen years after launch, though, the most successful franchise spinoff has nothing to do with Microsoft. Instead, it’s a very funny, long-running webisode series called Red Vs. Blue, created by Burnie Burns and Rooster Teeth Productions, inspired by Burns’ voice-overs of videos taken from his Halo gameplay. Peter Jackson and Neil Blomkamp were among the many attached to various Halo movie initiatives over the years with Fox and Universal. The estimable pair ended up instead making the fabulous District 9 together, reputedly incorporating some of the initial Halo visual-effects work by Jackson’s WETA team.

It’s true that Microsoft did commission a DVD full of anime short videos based on Halo, but who saw that? And the company recently announced that old-school gamer Steven Spielberg is now executive producer with Microsoft’s 343 Industries unit on a live-action Halo TV show. But that show hasn’t arrived yet, and there’s no guarantee that it ever will, given the franchise’s track record.

Halo is hardly Microsoft’s only misstep on a Hollywood Trail of Woe. Old-timers will recall Microsoft’s big 1990s investments in cable set-top boxes that went exactly nowhere and their pricey acquisition of WebTV, which was designed to be your grandmother’s TV-based path onto the pre-Bubble Internet. WebTV later became MSN TV, which will shut down September 30, not that anyone, including Grandma, actually noticed. MSNBC is called that because Microsoft partnered with NBC in 1996 on a cable-TV and Internet venture. That partnership is now long dissolved, and the online site rebranded NBCNews.com.

It’s true that Hollywood’s peculiarities and relationship-driven business deals have flummoxed plenty of other tech firms. Apple has had some minor successes, in part because its co-founder sold Pixar to Disney, whose CEO is now on Apple’s board (and Steve Jobs’ widow remains one of Disney’s biggest shareholders). But a big win, like building a smart TV or TV appliance that carries all of Hollywood’s TV channels, hasn’t happened yet, for anyone, despite that interesting Sony-Viacom deal that reportedly is near completion.

In the meantime, will Hollywood miss Steve Ballmer? Not very much at all, and not nearly as much as Microsoft and Ballmer wish it would.