Diggs was in the early stages of his acting career when he was cast in "The Best Man." At the time, he had only starred in notable films like "How Stella Got Her Groove Back" with Angela Bassett and "The Wood" alongside Omar Epps and Richard T. Jones. However, he bolstered his reputation in the rom-com realm when he took on the role of Harper Stewart, bestselling author of "Unfinished Business" and certified troublemaker who nearly derailed his college best friend's wedding on account of a one-night stand with his bride.