Guest Stars Martin Cummins as Tom Keller Nathalie Boltt as Penelope Blossom Jordan Connor as Sweet Pea Cody Kearsley as Moose Mason Robin Givens as Sierra McCoy Trinity Likins as Jellybean Jones Gina Gershon as Gladys Jones Co Starring Bernadette Beck as Peaches 'N Cream Matthew Yang King as Marty Mantle Simon C. Hussey as Major Marcus Mason Veena Sood as Headmistress Patricia Nneka Croal as Juliard Recruiter Michael Taylor as RROTC Cadet Uncredited Casey Cott as Teen Tom Keller Cody Kearsley as Teen Marcus Mason