City on the Edge of Forever (a.k.a. Flashbacks) - S2-E7
Question: Why is there a "missing" flyer for Macaulay Culkin?
Answer: I think it's just a joke about how out of work and the limelight he had been. This episode aired in 1998. From '88-'94, Macaulay had been in 14 movies, 3 TV shows, 2 music videos, and appeared on over a dozen shows as himself (SNL host, late-night talk show guest, etc). After "Ritchie Rich" in 1994, he wasn't in anything or on TV. So he was nowhere to be found for 4 years. Although, prior to the airing of this episode, he did appear in Sonic Youth's "Sunday" music video. But I think this episode was created before the release of the video.
Question: For the slightly crude ball-throwing game, why is Jennifer Love Hewitt the target?
Answer: In the late 90s and 2000s, she was reported to be dating several different men. She was often called a "serial dater."
Answer: He doesn't. The whole point of the scene is to satirise legal arguments, in that Cochran is basically talking complete nonsense in order to bamboozle the jury into taking his side, distracting them from the real issue with a barrage of red herrings.
Tailkinker ★