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.
Full Circle integrates the indigenous and modern practices, bringing individuals, community and organizations together as indispensable collaborators realizing a co-creative, sustainable and fulfilling future. He is famous for playing in several television series and films including the role of Reid in the series, Party of Five.
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), where he played a single teenaged father in love with Jessica Biel's character Mary.
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