A Texan attorney and political speech writer who opted for a career change in 1979 by moving to L.A. to attend USC's film school, Reynolds went on to become a sporadically successful Hollywood writer-director, often in stormy but productive collaboration with actor-producer Kevin Costner. His student film "Proof" was expanded to make his feature directing debut, "Fandango" (1985). Described by Brit culture mag Time Out as a "buddy coming of age road movie", the film featured an early lead performance by Costner. While "Fandango" garnered some affectionate reviews, it failed to register at the box office. The year before, Reynolds made his feature screenwriting debut (and received his first story credit) with John Milius' notorious Cold War fantasy "Red Dawn" (1984). His second directorial outing, "The Beast/The Beast of War" (1988), met with a mixed critical reception but remains notable for its depiction of the Soviet invasion of Afghanistan.

Reynolds reteamed with Costner for "Robin Hood: Prince of Thieves" (1991), which transcended bad notices to become a blockbuster hit. Costner served as executive producer for Reynolds' boldly campy period action film "Rapa Nui" (1994). Barely released in the USA, the film earned some kudos for its glorious display of beautiful bodies (including stars Jason Scott Lee, Esai Morales and Sandrine Holt), its assured deployment of widescreen imagery and what reviewer Dave Kehr described as "Reynolds' incredibly fluid, unpredictably ironic direction".

Reynolds joined forces with Costner again to helm the lavish futuristic underwater action flick "Waterworld" (1995). Industry insiders closely followed tales of its innumerable shooting delays, mishaps and an historically escalating budget (rumored to be as much as $180 million). The production suffered another blow when the director quit during post-production just three months before "Waterworld" was to be unveiled before the public. Reportedly, this dramatic exit was the culmination of a series of creative battles between Reynolds and Costner over the editing and content of the film. Neither Costner nor the studio, Universal, believed that the director's cut was worthy of test-screening so Reynolds walked (or swam) away. "Waterworld" went on to earn over $80 million, a respectable figure for most features, but not this film whose costs made it one of the most expensive films in Hollywood history to that date.

It took Reynolds a couple of years to regroup, but he returned to features at the helm of the "187" (1997), a drama about a high school teacher who gradually becomes unhinged after being attacked. Reynolds' direction was more than adequate but a convoluted script undercut the film's overall intention and left audiences disinterested. After another four years, the director was back on the big screen once again, this time directing a new take on an old classic, the much-filmed "The Count of Monte Cristo" (2001), teaming James Caviezel (in the title role) with Guy Pearce (as his archenemy).