Casting What-Ifs
Rob Lowe as Richard; Adam Sandler as Richard; Matthew McConaughey for the Lowe role; Roseanne Barr as Helen
In the discussion (4)
Approx. transcript time · 00:58:37Read transcript
- As the hosts tell it, Michaels originally envisioned Farley with Lowe as the foil in the Richard part, which fell through because Lowe had other commitments. — Bill Simmons
- The hosts say Farley pushed for Spade or Sandler; Sandler was already shooting Billy Madison, so Spade was the third choice, called the right one. — Bill Simmons
- The hosts say scheduling conflicts nearly forced Lowe out, and quick auditions included Matthew McConaughey, which would have been fun between Dazed and Confused and A Time to Kill. — Bill Simmons
- Helen the waitress was reportedly meant for Roseanne Barr, who was busy with her show; called a good miss. — Bill Simmons