Jake Gyllenhaal - Stronger

Reader find. From the Newplaidpants site.

Jake Gyllenhaal - "Bubble Boy"

I suppose these are some weird amalgam of tighty whities and colored briefs. Honestly I have no idea what are on these briefs. Boy, he looks young here.

Jake Gyllenhaal - "Love and Other Drugs" - 2010 - NSFW

Horrible movie (IMO), hot guy. Couldn't resist throwing in a bit of nudity for Jake.

Jake Gyllenhaal - "Highway" - 2002

Blink and you'll miss it scene.