He had guest parts on numerous television shows before being cast on the TV drama Party of Five (1994).
That same year, he landed another recurring role on 7th Heaven (1996), the WB's longest-running series, on which he played a single teenaged father in love with Jessica Biel's character Mary.
I didn’t want to fall too quickly and get my heart broken again.
You could talk to two or three girls at a bar and pick the best one, or you can swipe a couple hundred people a day—the sample size is so much larger. Crew; senior at Parsons; junior at Pace; works in finance …
In 1997, she was cast as Meadow Soprano, daughter of New Jersey mob boss Tony Soprano.
The show premiered in 1999 and became a huge success, catapulting Sigler to fame as a TV actress.
Keegan was then cast in two modern-day Shakespearean film adaptations: as the antagonist of Heath Ledger in the 1999 comedy 10 Things I Hate About You (adapted from The Taming of the Shrew) and as Mekhi Phifer's best friend in 2001's O, adapted from Othello.
Keegan then took a role in Greg Berlanti's The Broken Hearts Club: A Romantic Comedy (2000), which won best picture that year at the GLAAD Awards.