The first contestant is John Worek
- $2,500 Category Motown, 1964, Four Tops, “Baby I Need Your Loving”.
- $5,000 Category Duets, 1976, Elton John and Kiki Dee, “Don’t Go Breaking My Heart”.
- $10,000 Category Let’s Dance, 1964, The Beatles, “Twist and Shout”.
- $25,000 Category Pop, 1972, Johnny Nash, “I Can See Clearly Now”.
- $50,000 Category The Day the Music Died, 1957, Buddy Holly and the Crickets, “That’ll Be the Day”. He misses the song and leaves with $25,000.
The second contestant is Debra Toscano
- $2,500 Category Love Songs, 1976, Heatwave, “Always and Forever”.
- $5,000 Category Pop, 1983, Billy Joel, “Tell Her About It”. She uses her two words help.
- $10,000 Category 1980′s, 1987, Belinda Carlisle, “Heaven Is A Place On Earth.”
- $25,000 Category Rock, 1964, The Rolling Stones, “Time Is On My Side”.
- $50,000 Category Divas, 2000, Christina Aguilera, “What A Girl Wants”. She uses her three lines help.
- $100,000 Category Bee Gees, 1977, Bee Gees, “More Than A Woman”.
- $200,000 Category One Hit Wonders, 1980, Devo, “Whip It”.
- $350,000 Category R&B, 1964, Little Anthony & The Imperials, “Goin’ Out Of My Head”. She uses her backup singer. She walks away with $200,000.
