In time, Chris began composing original material for the Free Design to perform, and with the assistance of their father, the siblings cut a demo, ultimately signing with producer Enoch Light's audiophile label Project 3. The title track from their 1967 debut LP Kites Are Fun was also their first single, cracking the Top 40 on the Billboard adult contemporary chart but reaching only number 114 on the pop chart -- somewhat amazingly, it was the Free Design's biggest hit. Another Dedrick sister, Ellen, joined the group after graduating high school, making her debut on 1968's You Could Be Born Again. "2002: A Hit Song," from 1969's Heaven/Earth, satirically addressed the Free Design's continuing inability to make a commercial impact, but still the group's chart woes continued, and with their next effort, 1970's Songs for Very Important People, they targeted a new audience: children.

Stars/Time/Bubbles/Love, also released in 1970, returned the Free Design to their adult constituency; after issuing One by One two years later, the group was dropped by Project 3, at which time they relocated from New York to Canada. There Chris Dedrick recorded a solo album, Be Free, which went unreleased; signing to the Ambrotype label, the Free Design recorded one final LP, 1973's There Is a Song, before disbanding in 1975. In the years to follow, Chris remained the most musically active sibling, forming the choral ensemble Star Scape Singers, as well as arranging and composing for the Canadian Brass. He also won a series of Gemini Awards for his scores for Canadian film and television productions. By the '90s, hipster favorites including Cornelius, Pizzicato 5, and Louis Philippe were regularly citing the Free Design as a key influence, resulting in the 1998 release of Kites Are Fun: The Best of the Free Design. The new millennium saw the Free Design convene for another album -- 2001's Cosmic Peekaboo -- which gathered Sandy, Chris, and Bruce Dedrick back together again.