Bill Gates kicked off his world tour to promote Windows Vista’s worldwide retail release by appearing on the Jon Stewart’s Daily show. This promised to be an interesting meeting as Gates isn’t known for irreverent conversation. Stewart gave the Gates appearance a double sized interview slot. Most of his interviews appear after the final commercials for the last segment only. Only a few interviews get final two segments before the Stewart introduces Colbert’s show which follows.

The conversation was snappy and Gates appeared comfortable against Stewart’s goading wit. Not surprisingly some of the exchanges appeared scripted. Stewart picked up the issue of security flaws in Microsoft products. He asked how Microsoft can outsmart a worm created by a Danish 13 year old hacker. Gates joked that they hire 14 year olds. This was Gates segue into a few of the key Vista security features including web filters and parental controls.

The interview was a bit thin on laughs but it was an historic meeting. It seems that Jon Stewart has become a sort of establishment gateway to the perceived hip young demographic. Politicians have tolerated the Daily Show’s interviews for years and now cultural icons in need of a lift are reaching out to Stewart. Last year it was the Oscars and this year it’s Bill Gates and the Windows operating system.

Windows has taken a beating lately seeing much of its dominance under attack from upstarts like Linux. This is mainly because of the dominance the Internet has on the operating system experience. The current software - as - service computing paradigm threatens Microsoft. It’s probably no accident that Daily Show’s own John Hodgman appears as the PC in the famous “I’m a Mac” ads. The new version of Windows is likely to be released to more yawns than cheers. Compared that to the Windows 95 retail release where people were lining up at midnight to get a copy. This release is likely to be a disappointment.