Cannon's professional career began with adverts for James Garrett and later RSA. This led to his debut feature The Young Americans (1993), he signed on to direct the big-budget film Judge Dredd (1995), starring Sylvester Stallone, which was poorly received by critics and audiences alike. Since then he has also directed Phoenix (1998) and I Still Know What You Did Last Summer (1998), the latter of which was also poorly received by critics but still financially successful.