"I believe if people can listen to the albums, they tend to buy them," Richards said in a 2006 interview with Chicago Reader.

[2] Artists who have recorded on the label include Double Dagger, Future Islands, Tortoise, The Sea and Cake, Bummer, High Places, Trans Am, Mouse on Mars, ADULT., Bosse-de-Nage, Nobukazu Takemura, Bobby Conn, Tom Verlaine, Freakwater, The Zincs, The National Trust, Eleventh Dream Day, Califone, Chicago Underground Duo, Howe Gelb/Giant Sand, Mary Lattimore, Oval, Town & Country, Archer Prewitt, Sam Prekop, The Lonesome Organist, OOIOO, Pit er Pat, Marisa Anderson, The Fiery Furnaces, Angela Desveaux, Liturgy, Boredoms, Pontiak, and Golden Void amongst others.

In 2007, Thrill Jockey bands old and new recorded songs for a boxed set to celebrate the label's 15th birthday.

Plum 7" Box Set compilation was released in December 2007 on ten 7-inch vinyl singles.

Some notable tracks include: Directions covering Tortoise guitarist Jeff Parker's "Toy Boat", while Pullman tackles the Chicago Underground Quartet's "3 A.M." Bobby Conn, Califone and Thalia Zedek all cover Freakwater songs, while the Sea & Cake reworks a version of Califone's "Spider's House".