He then returned to Virginia, where he opened up a cabinet-making business with his brother Joe in 1974 in Abingdon.[5] He continued to act in community theater while he worked with his brother for several years.[5] Cress married Phebe Fullerton and the couple eventually moved to Fincastle, Virginia, where Cress' shop currently is.[7] Cress left his business with his brother and began creating his own furniture and opened his own shop.[5] Cress was inspired by furniture he found in different antique shops.[3] Cress continued his acting career in local theaters and he played the marshall in the 1993 movie "Sommersby."[4]
The first piece of animated furniture that Cress created was "Crippled Table," named by a friend of Cress' who had a leg damaged by childhood Polio.[4] The table has one leg replaced by a carved crutch. His other pieces include a clock based on the "Hickory Dock," nursery rhyme, called the "Hickory Dickory Dock Clock," one of which was sold through Sotheby's and another of which is in the Indianapolis Children's Museum.[6] "How to Build Furniture," a table with one shorter leg resting on a book and "Peel Here," a table that appears to peel back revealing a checkerboard, are other works. Cress has also animated other chairs through his "Self Portrait," chairs: chairs that are animated and appear to be building themselves.[6]
Cress' chair "Oops!" is the most famous of his animated furniture and the ninth one Cress created was displayed in the Renwick Gallery, Smithsonian Museum[8] and is now in the museum's permanent American Furniture collection.[5] "Oops!", made in 1991 is featured in the permanent collection of Yale.[6] "Oops!" is a Chippendale-style chair that is animated, including legs that have claws holding the traditional balls at the bottom of the chair in place.[5] One of the claws has lost its ball, leading to the name "Oops!". Other features of the chair include eyes and a slanted chair frame and legs. Cress made 10 of the "Oops!" chairs, all but one of which have been sold.[5]
Cress has been featured in The Washington Post[9] and American Art Magazine and is featured in the Virginia tourism site under "The Arts.[6][10] "
In 2011, Cress had an exhibition featuring his work in Abingdon, Virginia at the William King Museum. The exhibition was titled "Mischief-Making: Contemporary Craftsman Jake Cress," and included a carving workshop.[3]
Cress collaborated with painter Mark Young to create "The Decorator," a realist oil painting that extends outwards physically[6] through hand crafted furniture.[11] From the painting, a chair's arm, created by Jake Cress, reaches out and places a flower into a vase that rests on a table built by Cress. The table stands under the painting. The chairs featured in the painting are Cress' animated chairs. "The Decorator" was featured at the King William Museum.[7]