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Al Franken as Stuart Smalley (right) with "Muggsy B." and "Charles B."

Stuart Smalley is a fictional character invented and performed by actor, comedian, author, and political activist Al Franken. The character originated on the television show Saturday Night Live, in a mock self-help show called "Daily Affirmations With Stuart Smalley."

The character was a spoof on individuals who are obsessed with twelve-step programs 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. One character who becomes a romantic interest in the novel appears in the movie, where the character is played by a man — however, in the movie, nothing indicates that the two characters ever meet outside the courtroom, let alone develop romantic interest in each other.

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 (very often celebrities) to work out what he wrongly perceives to be their problems. In fact, 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.) In the end he almost always ends up breaking down and putting himself down, and the guest usually ends up comforting him instead.

The character was popular enough to spawn a novel, I'm Good Enough, I'm Smart Enough, and Doggone It, People Like Me!: Daily Affirmations With Stuart Smalley. The book keeps in line with the concept of the character, and is presented (tongue-in-cheek) as a legitimate day-to-day affirmation book. Each page is dated and the reader is "supposed" to follow through as if they were actually seeking help. Naturally, however, things go wrong in the writing process, and thus the affirmations branch off into Stuart's own commentary about what a hard time he is having writing it, etc. He also discusses his past relationship with ex-significant-other Dale, "the Rageaholic".

An audiobook was also released, You're Good Enough, You're Smart Enough, and Doggone It, People Like You. The content of this audio book was completely different from the printed one, but followed through on the same gag. The tapes played guided visualizations meant to help the listener relax and focus; however, Stuart makes a vow at the beginning not to make any edits or corrections in the recording process because "I'm a perfectionist and if I start making changes, I'll never stop." As such it is full with humorous errors, including one gag in which Stuart tells his listeners who are driving to work to "close their eyes and envision..." something. (As such, there is a warning label on the box that says, "Do not listen while driving," a joke that doesn't make sense until one has actually listened to the tape.)

As the character's popularity increased, a film was released called Stuart Saves His Family. It chronicled the life Stuart leads and his relationship with a very dysfunctional family. His alcoholic father and enabling mother, overweight sister and equally alcoholic brother call upon him when an aunt dies. He is asked to oversee the sale of her home, bringing much-needed money to all of the family. At the same time, his public access self-help show is cancelled. Naturally, things go amok, and he must learn to deal with himself and his own life before he can attempt to help others. While many critics praised the film, including Roger Ebert and Gene Siskel (who awarded the film 3.5 stars out of four, in his print review), the film was financially unsuccessful.

In Franken's book Why Not Me? The Inside Story of the Making and Unmaking of the Franken Presidency, Franken states that the character of Stuart Smalley is based on one Stewart Smiley, whom he met at an Al-Anon meeting.

The character effectively disappeared after the box-office failure of the film and Franken's exit from Saturday Night Live, save one appearance where Smalley, bitter over the failure of the movie, refused to finish his affirmation, excoriated his viewers for not watching, and openly wept. Al Franken did do the character again when Al Gore hosted, and the character shows up from time to time on The Al Franken Show.

Bill O'Reilly now refers to Al Franken as Stuart Smalley rather than calling him by his actual name.

The character is known for a number of catchphrases, many of which are chosen not just for comic effect, but to play on a perceived tendency of the self-help movement to talk and think in psychobabble. Some, such as the phrase "stinkin' thinkin'", are taken from common 12-step slogans.

• "That's just stinkin' thinkin!"
• "You're should-ing all over yourself."
• "Denial ain't just a river in Egypt!"
• "I'm good enough, I'm smart enough, and doggone it, people like me."
• "I am a worthy human being."
• "...and that's...okay."
• "(Wearing a halloween costume) I thought about going as a feeling, but what does dread look like really? Other than my mother."
• "I'm gonna die homeless and penniless and twenty pounds overweight!"

• Recurring Saturday Night Live characters and sketches