In mid-1985, 23-year-old Jason Scheff joined the multi-platinum band Chicago, after Peter Cetera had departed the band to continue his solo career. Scheff was noted for his uncanny vocal resemblance to Cetera. His lead vocals were debuted on the 1986 single "25 or 6 to 4," a remake of their 1970 hit, then followed up with "Will You Still Love Me? ». Jason amicably left Chicago in 2016.
Scheff has recorded as a solo artist a CD titled Chauncy in 1996, as well as several duets released only in Japan.
More recently, Scheff toured in late 2019 with Todd Rundgren, Micky Dolenz, Christopher Cross and Joey Molland of Badfinger in celebration of The Beatles White Album on the "It Was Fifty Years Ago Today – A Tribute to the Beatles’ White Album".