This strip was done just after the 2004 Presidential election in which George W. was voted back in as president of the USA. You're supposed to think the Xbox is being political, but of course he isn't. Why would he be sad that Bush was re-elected? He's a Microsoft product and the Republicans like big business.
Since launch, the Xbox has been defined by Halo, so naturally, the system would be sad that he'll have to wait quite awhile before the next one arrives. Unfortunately, what we didn't know back when the strip was created was that Halo 3 would be developed for the Xbox 360 and NOT the Xbox. Please don't tell the Xbox that. I doubt he could take that kind of bad news at this point.
The PS2's encouraging remark about a Killzone port sort of loses its impact now, due to the fact that the PS3 version of Killzone shown at E3 2005 was a hype-machine. When the strip was created Killzone had just kind of fizzled on the PS2 and wasn't the Halo killer it had been expected to be.
Things to note: