We had all but forgotten about that cute little kid from Jerry Maguire.

But Ray Boyd came back into our lives last night after an emailer sent over a photo from the recent Playboy Golf shenanigans where (real name) Jonathan Lipnicki (turns 20 in October) had some fun with the ladies. (Watch this. It’ll make you feel old.)

Anyway, this isn’t Jon’s first rodeo with Hef’s ladies. This lucky shit turned one movie part into the greatest chick getting ventures in Hollywood history.



The very top photo is from the 2010 Playboy Golf tourney.

We’ve also snagged two pics from the 2009 tourney where 18-year-old Jon partied it up right alongside the Hef girls. Let’s see, at 18 we were just praying to get laid as a college freshman.

This kid walks into the Mansion and has the audacity to go with the undone smoking jacket.

Jerry Maguire money still must be good because Ray Boyd hasn’t worked very much since 1996. A look at his IMDB shows that starring roles have been few and far between. Stuart Little 2 was eight years ago.

Still, all that matters for a child actor is that one role that will forever be a panty dropper. Jon is like a Doug Williams. Doug wasn’t a Hall of Famer but he has that Super Bowl ring. You’re never taking that away from him. Jon has that dorky little cute kid role and he’s going to use it, from the look of things, as a poon broom for years to come.

Congrats, kid.

[Official Jonathan Lipnicki Website]