Raphael began her comedy career writing and performing with the Upright Citizens Brigade Theatre (UCB) in New York and later in Los Angeles. Among her best known work at UCB, was the long-running Sketch show Rode Hard and Put Away Wet, written and performed alongside her comedy partner and best friend Casey Wilson; the stage show ran from 2003 to 2006 in New York and Los Angeles and was an official selection at 2005's US Comedy Arts Festival in Aspen, Colorado. The two women, who had first met in a clowning class during their freshman year at NYU, went on to win the ECNY Award for "Best Comedy Duo" in 2005. They also performed as members of the UCB improv teams "Mr. and Mrs. All-Star", "Sentimental Lady", and "Hey, Uncle Gary!". Raphael and Wilson's comedic partnership has since branched out into an active writing career in film and television, they co-wrote their first screenplay for the comedy Bride Wars, which they also appeared in with supporting roles, followed by landing a development deal with UPN in 2005 to create a half-hour comedy pilot and in 2007 they worked as Writers and story editors on the Americanized version of Creature Comforts on CBS. They also continue to contribute comedic videos to the humor website Funny or Die.