Episode 82 of "Will and Grace"
s04e11 Stakin' Care of Business

At the gym, Will spies another guy who looks maddeningly familiar, while Jack gets a workout as he keeps repeating one of his nonsensical catchphrases in hopes of seeing it become popular among the sweat set. Meanwhile, Grace gets some bad advice from Karen when she seeks a loan to expand her company so she stoops to asking her wealthy employee herself for the money—even if she has to resort to drastic measures to get the point across.