Joseph Gordon-Levitt
Then: He first captured our hearts as Roger in Angels in the Outfield, but reached official heartthrob status as nice guy Cameron in 10 Things I Hate About You. In 2000 he took a break from his acting career to attend Columbia, and when he came back he killed it in movies like 500 Days of Summer and Inception. In 2013 he wrote, directed, and starred in Don Jon.
Now: Watch him in the upcoming film Snowden as Edward Snowden and biographical drama The Walk. This self-declared feminist is married to Tasha McCauley, founder and CEO of a robotics company. JGL founded production company hitRECord, which has successfully produced short films.
[Photos via @daniipackman and @ejo2]