From his first big film role as Bob Sugar in Jerry Maguire I thought this guy was going to be a huge star. Then he did a bunch of stuff I never heard of (The Brave Little Toaster to the Rescue, Speaking of Sex, Black River, Cherry Falls - and the list goes on and on, but I'll spare you). After a 33 episode stint on Ghost Whisperer, he now has his own show, Gary Unmarried. While his career may be having a comeback, that will can never be said about his hairline...
Here's Jay in 2006:
And here's Jay with wife Nikki Cox (Las Vegas) about a week ago at a Knicks game: