Plans for "The Mask II" were in the works years before this film. Nintendo Power magazine held a contest, and first prize was a walk-on role in that movie. The project was canceled, and Nintendo Power's final issue included a public apology to the contest winner. Years later, the winner was revealed as Nathan Ryan Runk, from Arbutus, Maryland. The film was technically on hold, so Runk could have chosen the role or money and merchandise. Runk, who was 12 at the time, chose the money, and received $5,000, a film crew jacket (which he later lost), and several Super Nintendo video games, including "Pilotwings 64" on Nintendo 64. He later claimed it was "absolutely the right call."
Film critic Richard Roeper admitted that in the five years he co-hosted with Roger Ebert, this film was the closest he'd come to walking out halfway. Looking back, he wishes he'd walked out.
When asked why he agreed to do the film, Jamie Kennedy responded, "I'll give you 2.5 million reasons."
The film was initially intended as a follow-up to the original, with Jim Carrey returning as Stanley Ipkiss. Carrey decided after making Ace Ventura 2 that playing the same character twice wasn't interesting to him at the time, so the sequel was shelved, and this stand-alone film was developed instead. Carrey later became more open to sequels, costarring in Debi e Loide 2 (2014). In 2020, he said he wanted to do sequels to The Mask and Sonic the Hedgehog.