"Gmail Man" is the single greatest Microsoft ad ever made, but it isn't even an ad. Instead, it's a humorous internal video, aimed at Microsoft's own sales people, that positions its Office 365 service as a better alternative to Google's Gmail. The rationale is simple: Google reads every single email message that passes through Gmail and then generates context-sensitive ads that appear in the Gmail web client. This policy is at best suspicious, the Microsoft video implies, and with great humor.
"He's everywhere and nowhere at the same time," the video says in a sing-song fashion as a humorous looking character, "Gmail Man," appears onscreen in an outfit reminiscent of a postal worker. "He peeks at every subject in un-real time. Probing every sentence and all your punctuation. Got his nose in every colon and every situation. He's the Gmail Man!"