After making his feature film debut in City Slickers at just 10 years of age, Jake Gyllenhaal went on to appear in several movies throughout the decade before truly breaking through in pictures like ...

Both are Hollywood A-listers whose high-profile relationships have taken up a lot of bandwidth over the years, so perhaps it was inevitable that one day Reese Witherspoon and Jake Gyllenhaal would get ...

When you furrow your brow and think back to early ‘aughts celebrity relationships, you might find yourself pondering “Did Kirsten Dunst and Jake Gyllenhaal really date or does it just seem like they ...