His death was the first time that Ed Wynn ever made anyone sad.

Red Skelton’s line is an affectionate epitaph for fellow comedian Ed Wynn, built on the premise that Wynn’s public persona was so relentlessly gentle and funny that he never caused sorrow—except by dying. The humor depends on inversion: death, normally treated with solemnity, is framed as Wynn’s only “failure” to make people happy. It also gestures toward the cultural role of entertainers as emotional caretakers, whose passing can feel like a personal loss to audiences. As a tribute, it compresses admiration (Wynn’s gift for joy) and grief (the sadness of his absence) into a single, memorable quip.