Guest Stars Jeff Hiller as Phil Miller Brendan Clifford as Grady Dupont Karl Gregory as Marcus Rice Cherie Corinne Rice as Malik Walker Jacob Wallach as Randy Wolfe Jordan Clifford as Brady Dupont Ashley Park as Olivia Cho Barbara Tirrell as Sonya Yenin Kelly Rutherford as Herself Brooke Shields as Herself Edan Alexander as Jimmy 3 Jackson Frazer as Homeless Child Cadden Jones as Woman Jadyn Tattoli as Jimmy 4 Graydon Yosowitz as Jimmy 2 Juju Chang as Herself Peyton Lusk as Jimmy 1