My mother and father were very strange people. They tried to be

“My mother and father were very strange people. They tried to be funny which is always very sad to me.” Thus spoke Jonathan Winters, the jester-philosopher of his age, a man whose laughter carried the weight of sorrow, and whose humor often masked deep reflection. In this confession, he unveils a truth that pierces the heart of comedy itself—that beneath the desperate attempt to amuse, there often hides loneliness, insecurity, or the quiet ache for love. His words are not scorn, but lament: a recognition that when laughter is forced, it becomes not joy, but disguise.

When Winters calls his parents “strange,” he is not speaking of cruelty or madness, but of souls who wore masks to survive. To “try to be funny” is to seek acceptance through performance, to beg for warmth by way of laughter. In childhood, he saw this and understood—perhaps too soon—that the joke can sometimes be a cry for connection. What he calls sad is not the humor itself, but the emptiness that births it when it comes not from delight, but from need. In his own life, this understanding became both a wound and a gift. It shaped him into one of the most original comedians of his generation—one who knew that laughter could heal, but also that it could hide deep pain.

The origin of this quote lies in Winters’ early life—a childhood marked by instability, by separation, and by longing. His father left the family when Jonathan was still a boy, and his mother, struggling to rebuild, sought solace in levity. She tried to make light of what was heavy, to turn the unbearable into a jest. But to her sensitive son, the laughter rang hollow, and the effort itself became tragic. For the young Winters, humor became both inheritance and burden: he learned that comedy, when divorced from truth, can sound like sorrow wearing a smile. And yet, he also discovered that through honest laughter—born not of denial but of courage—one could rise above pain.

The ancients too knew this paradox. The Greeks told of Democritus, the “laughing philosopher,” who found joy in the folly of mankind yet wept in private for its blindness. His laughter was not mockery, but a shield against despair. In every age, those who see too deeply must choose how to face the absurdity of life—some with tears, others with laughter, and some, like Winters, with both. His parents “tried to be funny,” but lacked the freedom of spirit that true humor requires. For authentic laughter is born not of effort, but of understanding; it arises when one has looked upon suffering and still chosen to smile.

Winters himself transformed that sad inheritance into art. On stage, he became a thousand voices—a trickster, a storyteller, a shape-shifter. His improvisations, wild and unpredictable, came from the deep well of his imagination, which he had dug as a child to escape loneliness. But unlike his parents, his humor was not a mask—it was a bridge. Through laughter, he reached others, and through them, found healing. His genius was to turn the sadness of forced laughter into the beauty of spontaneous joy, to teach that comedy need not hide pain, but could transform it into light.

There is, in this quote, a warning for all who seek to make others laugh or to comfort through performance. Do not mistake humor for happiness, nor effort for connection. True laughter cannot be faked; it is the music of the soul when it recognizes truth. When we “try to be funny” out of fear, we distance ourselves from others; but when we laugh out of love and humility, we draw them near. Winters’ sorrow for his parents was not condemnation, but compassion—for he understood that they were simply seeking to be seen, to be accepted, to matter.

So, dear listener, take this wisdom as your own: let your laughter be honest. Do not perform joy to hide your sorrow, nor force humor to earn affection. Let your smile rise naturally, as a flower opens to the sun. When life grows heavy, laugh not to escape, but to endure. And when others try too hard to be funny, see not their failure, but their longing. Offer them kindness instead of judgment, listening instead of applause.

For as Jonathan Winters teaches through his quiet truth, the saddest laughter is that which hides the heart—but the truest laughter, born of empathy and courage, is the one that saves it. Let us, then, be both wise and kind: to laugh deeply, to love sincerely, and to remember always that joy is not something we perform—it is something we become.