In 1998 Shankman wrote and directed "Cosmo's Tale", a non-dialogue short film that appeared at the Sundance Film Festival. Following the short, his sister, Jennifer Gibgot, asked him to read a script that she had already set up with Fine Line Features, entitled "The Wedding Planner". He liked the script and this led to a meeting with execs. He was hired for the job of director ten minutes into the meeting. The movie eventually went to Columbia Pictures and was a box office success.