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Nia Long as Lisa Wilkes, Will's girlfriend and later fiancée

Nia Long

Played: Lisa Wilkes, Will's girlfriend and later fiancée

Now: When Smith's eventual wife, Jada Pinkett-Smith, was considered too short to play Lisa, Long stepped in to take the role. She became a familiar face in movies and TV shows, from "Third Watch" to "Are We There Yet?" Recently, Long faced off against Don Cheadle in Showtime's "House of Lies" and she will reprise her role in the sequel "The Best Man Holiday" this winter.