Stiller had a few minor roles in the early 1990s, in films such as Stella, Highway to Hell and in a cameo, The Nutt House. In 1992, Stiller was approached to direct Reality Bites, based on a script by Helen Childress. Stiller devoted the next year and a half to rewriting the script with Childress, fundraising and recruiting cast members for the film. It was eventually released in early 1994, directed by Stiller and featuring him as a co-star. The film was produced by Danny DeVito, who would later direct Stiller's 2003 film Duplex and produce his 2004 film Along Came Polly.  Reality Bites debuted as the highest-grossing film in its opening weekend and received mixed reviews.  Stiller joined his parents in the family film Heavyweights (1995), in which he played two roles, and then had a brief uncredited role in Adam Sandler's Happy Gilmore (1996). Next, he had lead roles in If Lucy Fell and Flirting with Disaster, before tackling his next directorial effort with The Cable Guy, which starred Jim Carrey. Stiller once again was featured in his own film, as twins. The film received mixed reviews, but was noted for paying the highest salary for an actor up to that point, as Carrey received $20 million for his work in the film. The film also connected Stiller with future Frat Pack members Jack Black and Owen Wilson.  Also in 1996, MTV invited Stiller to host the VH1 Fashion Awards. Along with SNL writer Drake Sather, Stiller developed a short film for the awards about a male model known as Derek Zoolander. It was so well received that he developed another short film about the character for the 1997 VH1 Fashion Awards and finally remade the skit into a film.

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