[6] Wendy and Lucy was also placed at #87 on Slant Magazine's best films of the 2000s,[7] and also appeared on many "Top 10 Films of 2008" lists,[8] including those of the Chicago Reader, New York Post, Newsweek, The Austin Chronicle, LA Weekly, The Philadelphia Inquirer, the Seattle Post-Intelligencer, Entertainment Weekly, The New York Times, The Oregonian, Slate, The Village Voice, and The Christian Science Monitor.

In 2012, Raymond also published a second novel, Rain Dragon, which revolves around the character of Damon and his girlfriend Amy, who have had enough of Los Angeles and decide to leave the city to work on a community farm.

Raymond also wrote the screenplay for Reichardt's 2010 western Meek's Cutoff, which competed for the Golden Lion at the 67th Venice International Film Festival.

Raymond also co-wrote all the teleplays (all five episodes) for the 2011 five-part HBO miniseries, Mildred Pierce, directed and also co-written by Todd Haynes based on James M. Cain's novel, and starring Kate Winslet as the title character, as well as Guy Pearce, Melissa Leo, Evan Rachel Wood and others.

Raymond's professional duties include co-editing Tin House, editing Plazm, art criticism for Artforum and Modern Painters, and teaching through The New School.

Raymond produced the 2012 feature film, Buoy, directed by Steven Doughton and starring Matthew Del Negro and Tina Holmes.

Raymond used the name "Slats Grobnik" (a character created by Chicago newspaper columnist Mike Royko) when he worked as Haynes' assistant on Far From Heaven, and Roger Ebert noticed this deep in the credits and wrote about it in his "Movie Yearbook 2004.