Reeves attended the University of Southern California. There, between 1991 and 1992, he produced an award-winning student film, Mr. Petrified Forest, which helped him acquire an agent; he also co-wrote a script that eventually became Under Siege 2: Dark Territory. After graduating, he co-wrote The Pallbearer, which became his professional directorial debut.

Reeves directed the 2008 Monster movie, Cloverfield, which Abrams produced; Reeves produced the 2016 sequel to that film.

He also wrote and directed Let Me In, a remake of the Swedish film Let the Right One In, which was released on October 1, 2010 by Overture Films. He was a special guest at the 2010 San Diego Comic Con.

Since 2011, Reeves has been working on the script of 8 O'Clock in the Morning, a science fiction film based on the short story of same name written by Ray Nelson, previously adapted by John Carpenter as They Live. He will also direct the film and Universal Pictures will produce the film.

Critical, public and commercial reception to films Reeves has directed as of April 16, 2015.

In January 2017, it was reported that Ben Affleck had stepped down as Director for his co-written, co-produced, and self-starring, The Batman; while also naming Reeves as one of several filmmakers on a shortlist of those the studio and Affleck were jointly considering as a replacement to direct the film. In February 2017, it was announced that he would direct and produce the upcoming film. Production on the film will start sometime in June 2018, in Burbank, California. The film will exist inside the large and expanding DC Extended Universe.