In the late 80s his acting career slowed. He was a guest star on Who's The Boss?, Punky Brewster, The Wonder Years, and Highway To Heaven, and appeared in the film The Dirt Bike Kid, Carly's Web, Russkies and Beverly Hills Brats.
In the early 90s Billingsley played a would-be jock who gets hooked on steroids in the CBS Schoolbreak Special The Fourth Man. His next Schoolbreak Special appearance was in 1994's The Writing on the Wall, starring Hal Linden as a rabbi who teaches three boys about the horrors of intolerance after they are caught defacing his home, temple, and car with swastikas and anti-Semitic graffiti.
Also in the 90s he decided to start doing more work behind the scenes by producing, writing and directing. Known as Peter Michaelsen, he was assistant editor on the movie Knights. In 1994 Peter starred in, wrote, and directed (credited as Peter Billingsley) the short film The Sacred Fire, and credited as Peter Michaelsen in the executive producer function. Other behind the scenes work has included The Discovery Channel's A.R.K., The Adventures of Animal Rescue Kids, Patriot Son, The X Show, Made, and Elf, Dinner for Five Zathura, The Break-Up, and Iron Man; he also acted in the film, playing a scientist who works for Obadiah Stane. He also directed 2009's Couples Retreat.
Billingsley has also done a little acting recently in Sherman Oaks, Family Reunion: A Relative Nightmare, Elf, L.A. Heat, Four Christmases and No Deposit, No Return.
Billingsley has recently written a musical adaptation of A Christmas Story that is scheduled to open in Seattle during the second week of December 2010.
Before he was in A Christmas story he did a bunch of commercials. Billingsley's first acting role was as a two-year-old in a Geritol commercial. He went on to star in about 120 television ads throughout the 1970s and early 80s.He was probably best known for a series of commercials for Hershey's chocolate syrup in which he portrayed the character Messy Marvin.
He also played in several films like If Ever I See You Again, Paternity, Honky Tonk Freeway, Death Valley, Massarati and the Brain, and the made-for-TV movie Memories Never Die.