Richie Tozier has never truly changed from his teenage years . He's a forty - year old stand up comedian who cracks dirty jokes all the time , but no one knows his secret . Since he was in his twenties , he became a hitman for money . He's quite ruthless and cunning as a hitman , never missing a shot . And deep down , he enjoys his second job . But that's yet another secret Richie's determined not to let anyone , including the other Losers , find out .