I want to go out at the top, but the secret is knowing when you’re at the top, it’s so difficult in this business, your career fluctuates all the time, up and down, like a pair of trousers.

Stewart frames retirement and longevity as a problem of timing rather than talent: artists often aspire to “leave at the top,” yet fame is hard to measure in real time. His comic simile—careers rising and falling “like a pair of trousers”—underscores the volatility and embarrassment that can accompany public success and decline. The remark also hints at the music industry’s cyclical nature (hits, tours, critical fashion, aging audiences), suggesting that an entertainer’s “peak” is not a single moment but a moving target. The humor softens a serious anxiety: that staying too long risks diminishing one’s legacy, while leaving too early risks misjudging one’s own momentum.