By 1989, Chechik was ready to direct his first feature film, the frenetic Chevy Chase comedy "National Lampoon's Christmas Vacation." After one TV premiere ("The Big Room," 1990) and a handful of fizzled film projects, Chechik directed the quirky "Benny & Joon" (1993), a quiet, off-kilter romance starring a fey Johnny Depp, Aidan Quinn and Mary Stuart Masterston. The film did average business but received largely glowing reviews. Another quirky film followed. "Tall Tale: The Unbelievable Adventures of Pecos Bill" (1995) was a 1905-era fantasy about a young boy (Nick Stahl) and his encounters with the legendary Pecos Bill (Patrick Swayze), Paul Bunyon (Oliver Platt), John Henry (Roger Aaron Brown) and other Old Westerners. Beautifully lensed in Grand Canyon, Monument Valley, Death Valley and northern California, the film was "a lament for the passing of the Old West," according to the director.
Chechik's next film was a sharp change of pace: a remake of the new wave thriller "Diabolique" (1996), starring Sharon Stone as a vexed murderess and Isabelle Adjani as her partner-in-crime. Sadly, the film suffered in comparison to the 1955 original. Chechik's follow-up was a big screen version of the 60s TV series "The Avengers" (1998), with Ralph Fiennes and Uma Thurman assuming the roles made famous by Patrick Macnee and Diana Rigg.