I never understood why companies like that want to give more to those who have the most.

Because it's like a free endorsement. A teenager sees Britney in a photo showing off her free iPod in an impromptu publicity photo while waiting to talk to Joan Rivers for E! before the Grammys. So the teen bugs mom and dad to get her an iPod just like Britney has. A more appealing image than a needy child with a Saks bag for a school bookbag.