Estimated reading time: 6 minutes
What These Words Mean
You probably know that slightly guilty smile you get when something feels really good but also a bit wrong. There is a strange warmth in that moment: you feel human, flawed, and very alive. Alexander Woollcott captures that exact mood when he says: "All the things I really like to do are either illegal, immoral, or fattening."
First, you meet: "All the things I really like to do…" On the surface, this points to the activities that genuinely light you up. Not the stuff you do because you should, or because it looks good on a résumé, but the things that make you grin, relax, or forget the time. This part of the quote quietly admits that you have desires that feel strong and unmistakable. It hints at a deep hunger in you for pleasure, for release, for fun that is not measured or justified. It also suggests that the things you truly enjoy might not line up neatly with what the world praises as "disciplined" or "productive."
Then comes: "…are either illegal…" Now the scene shifts: activities that break the law, that cross clear external boundaries. Maybe you imagine speeding on an empty road at night, or doing something forbidden just for the thrill. On one level, this is a joke, exaggerating how "bad" your desires are. Underneath, it points to the human pull toward transgression. Sometimes you want to push past rules just to feel that you are not completely tamed by them. It speaks to the side of you that resents constant control, that aches for a pocket of wildness, even if you never actually act on it.
Next: "…immoral…" Here the focus moves from legal rules to the rules of conscience and social judgment. These are the things that might not land you in court but could bring shame, disapproval, or a sense of inner conflict. It nods toward fantasies, cravings, petty cruelties, or selfish pleasures you might not proudly announce. This part of the quote exposes how often your desires bump up against your values, or at least against what you think you are supposed to value. It can feel like your most vivid wants and your idea of being a "good person" are quietly wrestling with one another.
Finally: "…or fattening." Suddenly the tone lightens, and you can almost taste it: warm pizza, sugary pastries, that second bowl of ice cream late at night while the TV flickers softly in the dark. This part lands the joke, bringing the grand drama of law and morality down to the familiar struggle with food and body. It says: even when what you enjoy is harmless, it still seems to carry a cost. It captures the everyday frustration that pleasure often appears tied to consequence — weight gain, health worries, or just self-criticism. In my view, this is the most honest and tender part, because it touches how small and constant your negotiations with yourself can be.
Imagine you had a long, exhausting week, and on Friday night all you want to do is order greasy takeout, skip the gym, and binge your favorite show until 2 a.m. Nothing here is truly awful, but you feel that familiar internal courtroom: you "should" cook something healthy, "should" go to bed earlier, "should" not spend so much time on screens. These words reflect that inner tension. They exaggerate it into humor but do not deny the real weariness of feeling like everything deeply enjoyable comes with a warning label.
Still, the quote does not completely hold. There are things you really like to do that are neither illegal, nor immoral, nor fattening: holding someone you love, walking in the cold morning air, listening to a song that makes your chest ache in a good way. This tension is important. It suggests that while your mind loves to dramatize your desires as dangerous or forbidden, there are also quiet, nourishing joys that do not ask you to pay for them with guilt. The quote works best as a playful mirror of your self-criticism, one that invites you to laugh at how quick you can be to judge your own pleasure.
The Background Behind the Quote
Alexander Woollcott was an American critic, essayist, and radio personality active in the early 20th century, most famously associated with the Algonquin Round Table in New York. He lived in a time when public wit was a kind of social currency, especially in literary and theatrical circles. Clever one-liners, sharp observations, and ironic complaints were ways of both entertaining others and revealing something true about human nature.
The early to mid-1900s also held a lot of tension around pleasure and restraint. You had Prohibition in the United States, moral crusades, and strong ideals about respectability, especially in public life. At the same time, cities like New York pulsed with nightlife, theater, cabarets, and a growing culture of indulgence and entertainment. People were caught between strict social codes and a rising desire for freedom, enjoyment, and personal expression.
In that setting, a saying like "All the things I really like to do are either illegal, immoral, or fattening" made immediate sense. It poked fun at the heavy moralism of the era while also acknowledging how often people felt guilty for simply wanting pleasure. It allowed listeners to laugh at their own secret cravings and small rebellions, without having to confess anything specific. Even today, the quote survives because that push-and-pull between rules and enjoyment, between discipline and delight, is still very much alive in you.
About Alexander Woollcott
Alexander Woollcott, who was born in 1887 and died in 1943, was an American writer, critic, and radio commentator known for his sharp wit, theatrical personality, and deep involvement in New York’s cultural life. He began his career as a drama critic, becoming one of the most influential voices on Broadway, where his opinions could elevate or sink a show. He was a central figure in the Algonquin Round Table, a group of writers and artists celebrated for their humor, intelligence, and often biting conversation.
Woollcott later became a popular radio host, bringing his distinctive blend of charm, opinion, and storytelling to a wide audience. He loved wordplay and the kind of humorous exaggeration that reveals uncomfortable truths in a way people can actually hear. His public persona was a mix of curmudgeon and entertainer, someone who complained dramatically but with a wink.
The quote about everything enjoyable being illegal, immoral, or fattening fits neatly with his worldview. He often highlighted the absurdity of social norms and the gap between what people were told to value and what they actually wanted. In joking about the costs of pleasure, he was also giving people permission to recognize their own desires without taking themselves too seriously. His talent was in turning that recognition into laughter rather than shame.
