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’87
First breakout
At 15, he seemed destined for greatness after playing nerd-turned-cool guy Ronald Miller in the 1987 teen comedy “Can’t Buy Me Love.”
’87-2001
Rough patch
Between 1987 and 2001, bad films such as “In a Shallow Grave,” “Bank Robber” and “Coupe de Ville” landed him a spot on the D-list.
’90-2001
Guest roles
He turned up on TV shows such as “Will & Grace,” “Chestnut Hill,” “Jeremiah” and “Once and Again” during the 1990s and early ’00s.
2002
Second break
His role opposite Reese Witherspoon in 2002’s “Sweet Home Alabama” got him noticed again.
2005
Resurrection
In 2005, he was suddenly a heartthrob again after “Grey’s Anatomy” debuted.
[SOURCES: IMDB.COM]
