17. HEIDI MONTAG

When: 2008
Comment: "While I was watching this I was hoping a giant jellyfish would leap out of the ocean and sting one of her big, fake boobies!"

Spencer Pratt and Heidi Montag were the most easily ridiculed couple but the late 00s. Naturally, Handler made the quip after jokingly playing a clip of Heidi Montag's music video "Higher" on Chelsea Lately.