And while the segment is always awkward, it went to a whole new level when the "Hangover" star brought up Jennifer Aniston and Angelina Jolie ... in the same sentence!
"Is it hard for you to maintain a sun tan? Because you live in your wife's shadow," Zach joked. "I had a romantic fling that was public and it got on my nerves because she out-shined me."
"Tell me about the first time you saw Angelina ... was it like when Ross first saw Rachel?" he then said, directly referring to Pitt's ex-wife's "Friends" character. He then played some of the show's theme song.
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