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‘About Last Night’ With Bill Simmons, Chris Ryan, and Mallory Rubin

Bill Simmons, Chris Ryan, and Mallory Rubin revisit the 1986 romantic comedy 'About Last Night,' discussing its enduring legacy, Chicago's cinematic golden age, and the film's surprisingly frank portrayal of relationships.

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Bill Simmons, Chris Ryan, and Mallory Rubin gathered to dissect the 1986 romantic comedy 'About Last Night,' a film celebrating its 40th anniversary. The trio explored the movie's surprising depth, its impact on the rom-com genre, and its vibrant portrayal of 1980s Chicago.

The Enduring Legacy of 'About Last Night'

Simmons kicked off the discussion by admitting the film's significant personal impact. "This one really hurts because I remember where I saw it, who I was with," he confessed (02:44). He humorously added that he initially believed the movie provided a blueprint for relationships, only to later realize it was a "wrong blueprint" (03:02). Ryan highlighted the film's unconventional narrative structure for its time, particularly its depiction of the "beginning, middle, end, and then re-rise of a relationship in a movie" (03:07). He noted that 'About Last Night' felt closer to 'Annie Hall' than other contemporary rom-coms, praising its mature approach to relationships.

Simmons also revealed his unusual viewing habit: he watches 'About Last Night' at least once a year, a tradition he likened to Mallory Rubin's annual viewing of 'The Lord of the Rings' trilogy (05:28). Rubin confirmed her tradition, explaining it's a cherished holiday ritual with her husband. Simmons admitted that 'About Last Night' is one of the few movies he and his wife both love equally, placing it among a select group of fewer than 15 films (06:09).

Keep reading in The Digest

The full 4-minute article, 6 more sections, and every new episode from The Rewatchables and the creators you follow.

  1. Chicago: The Fifth Character
  2. The Dating Cycle and Unconventional Relationships
  3. Standout Performances and Unexpected Depth
  4. 'About Last Night' as a Rom-Com Pioneer
  5. The Brat Pack Era and Rob Lowe's Rise
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