Video of the week: "Bad Sinatra"

This is a new weekly feature where we’ll be reviewing an online video show or podcast every Friday. It’s our goal to introduce interesting content for all of our cool digital lifestyle devices, including iPods and PSPs, Apple TV, Windows Media Centers, gaming consoles, TiVo, even cell phones.

Steve Gillmor

I’m giving Steve Gillmor a mulligan on this one.

Steve Gillmor, the irascible technology journalist of ZDNet fame (and others), has finally returned to the podcasting airwaves with a wonderfully-named show called “Bad Sinatra,” only this time he’s wielding a camcorder, not a microphone.

When we last left Gillmor, he was curmudgeonly as ever as the host of the tech podcast “Gillmor Gang,” which was originally hosted on ITConversations and later Podshow. The sometimes-weekly show featured a Who’s Who of tech journalists — Doc Searls, Dana Gardner, Dan Farber, Mike Vizard, Jon Udell, and later Mike Arrington and Jason Calacanis.

Gillmor Gang
The Gillmor Gang

You either loved the show or hated it. I loved it. Hosted by the cantankerous Gillmor, the Gang was loosely scripted, very rough around the edges from content and production-value standpoints, and oftentimes frustrating to listen to because of the attitude and manipulative style of the host himself.

Yet buried in each show were wonderful nuggets of insight, discussion, and spirited debate — better than any I found in other tech podcasts. Gillmor was often at the forefront of ideas, pushing his guests to exasperation with relentless comments about Microsoft Office being dead, links being dead, how Gmail rules, and the fact that Google will crush Microsoft and Yahoo! I never kept score, preferring to look beyond his sensational statements at the meaning of what he was saying.

Seinfeld meets Gillmor in “Bad Sinatra”

Bad SinatraGillmor abruptly ended the Gang in November 2006, and I’ve missed him ever since. So I was delighted to stumble upon his latest venture, “Bad Sinatra”. The first episode “stars” Gillmor, along with Marc Benioff, Dan Farber, Mike Arrington, Robert Scoble, and Doc Searls. Farber says “Bad Sinatra” is Gillmor’s version of “Silicon Valley cinema verite.”

While I liked the show, I was ultimately disappointed because it was Gillmor acting like filmmaker Michael Moore. I didn’t even care that the video was rough, in need of editing, and the sound quality sucked. That’s Gillmor’s style. I’m used to it. He walks into Benioff’s offices at, orders about a receptionist (ala Moore), but to no end. Farber sums up the whole 38:30 program by saying, “You don’t have a plan. You just go point and shoot.”

Bad Sinatra Robert Scoble

Which may have worked for a podcast, but I am not sure it will for a video production. In “Bad Sinatra” Gillmor wanders from interview to interview with Benioff, Farber, Arrington (who looked totally annoyed), Robert Scoble, and Doc Searls — all A-listers in Silicon Valley — but performs his stale Microsoft/Google schtick, although he does update it a bit with quasi-questions about the new iPhone. At times it felt Seinfeld-ian, a show about nothing.

Gillmor says about “Bad Sinatra,” “No, it’s not the Gillmor Gang, but who cares.” I don’t. I don’t want Gillmor Gang 2.0. But a new show, particularly one moving from audio to video, demands progress, a stepping forward for our hero. Instead, he duffs his first shot off the tee.

“Bad Sinatra” is available in Flash video and mpeg4 at It’s also available for download at PodTech in video (mpeg4) and iPod formats and from Gillmor’s GestureLab blog. As per his quirky style, Gillmor does not offer (yet) a link to subscribe to the show.

last100 is edited by Steve O'Hear. Aside from founding last100, Steve is co-founder and CEO of Beepl and a freelance journalist who has written for numerous publications, including TechCrunch, The Guardian, ZDNet, ReadWriteWeb and Macworld, and also wrote and directed the Silicon Valley documentary, In Search of the Valley. See his full profile and disclosure of his industry affiliations.

3 Responses to “Video of the week: "Bad Sinatra"”

  1. Jamie says:

    I terribly miss the Gillmor Gang

  2. Marshall says:

    I miss the the GGang SO much! So does my dog, whom I never walk anymore. I hope this show will improve but it warmed my heart anyway.

    Great review btw and welcome to the site!

  3. slot pulsa says:

    Walaupun saya menyukai pertunjukan itu, saya akhirnya kecewa karena Gillmor bertindak seperti pembuat film slot deposit pulsa. Saya bahkan tidak peduli bahwa videonya kasar, perlu diedit, dan kualitas suaranya menyebalkan. Itu gaya Gillmor.

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