Guest Stars Andrew Rannells voices Matthew MacDell Richard Kind voices Marty Glouberman Joe Wengert voices Caleb Paula Pell voices Barbara Glouberman Kat Dennings voices Leah Birch Jon Daly voices Judd Birch June Diane Raphael voices Devin Jak Knight voices DeVon Jessica Chaffin voices Shannon Glaser Neil Casey voices Lars Gina Rodriguez voices Gina Alvarez Zachary Quinto voices Aiden Natasha Lyonne voices Suzette Michaela Watkins voices Cantor Dina Reznick Gil Ozeri voices Brad Piotr Michael voices Siamese Twin #2 Paula Pell voices Lola's Couch Pillow Mark Rivers voices Siamese Twin #1 Ileen Goldsmith voices Jessi Glaser - Singing Ileen Goldsmith voices Judd's Girlfriend Marisa Lark Wallin voices Reese's Wertherspoon Marisa Lark Wallin voices Woman