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Stuart Smalley is a fictional character invented and performed by satirist and later Senator Al Franken. The character originated on the television show Saturday Night Live, in a mock self-help show called "Daily Affirmation With Stuart Smalley." Stuart is Franken's middle name.

The character was a spoof on individuals who are obsessed with twelve-step program and become addicted to the actual act of going to therapy for addiction. Stuart is a member of many (sometimes fictional) twelve-step groups, including Overeaters Anonymous, Children of Alcoholic Parents Anonymous, and Children of Rageaholic Parents Anonymous. He is an effeminate man with a perfectly coiffed bleached-blonde hairdo, who regularly wears a yellow button down shirt with a powder blue cardigan.

It is frequently hinted that Stuart may be gay, but his sexual orientation is never clearly stated. All his romantic partners have names which could be male or female, like Dale, Chris, or Merle. His father gripes, "You'd drink too if you had Liberace for a son."

Within the context of the show, Stuart is quick to point out that he is not a trained therapist. However, he does his misguided best to help his on-air guests to work out what he wrongly perceives to be their problems. His guests are very often celebrities, however Smalley is seemingly oblivious to his guests' fame as he never uses their full names so as to "protect (their) anonymity." Smalley often projects his own problems onto others; thus he will attempt to solve an issue that is not really there. For example, in what many believe may have been the most amusing Smalley skit, he tried to help Michael Jordan resolve nonexistent doubts about his basketball-playing ability. While Jordan admitted it is natural to feel apprehension before games, he did not feel so scared he wanted to "lie in bed and eat Fig Newton". In the end he almost always ends up breaking down and putting himself down, and the guest usually ends up comforting him instead. In a couple of the later sketches the idea was reversed, where the guest appeared to be on top of the world and self-assured, but Stuart would unknowingly make a comment that would shatter the guest's aura of invincibility, such as Stuart innocently asking Charles Barkley that he must be glad at winning so many world championships. At the time of the episode's airing, the Phoenix Suns had recently failed to win the 1993 NBA Finals, which suddenly causes Barkley to break down in tears and admit he feels he is a big failure in life, to which Stuart is the one to comfort and reassure him.

Stuart Smalley has not been a contender in any CBUB matches.