The Biggest Age-Gaps in Celebrity Relationships Over the Years

In the late 1990s, James Woods began dating Ashley Madison, a college student with no connection to Hollywood. Their relationship quickly drew attention due to the stark age difference and Woods’s established status as a serious, veteran actor.

The romance was short-lived and ended quietly. Madison later distanced herself from the spotlight, while Woods moved on publicly. The relationship is now mostly remembered as one of Hollywood’s more uncomfortable age-gap pairings of the era.