Career Resurrection: After falling out of the Hollywood limelight in the early-2000s, Matthew Lillard's well-received role as the man Elizabeth was cheating with got him back on the radar and lined him up with several other dramatic live-action roles, including a stint on FX's The Bridge and playing antagonist to Clint Eastwood in Trouble With The Curve
Casting Gag: A running joke during the early parts of the book is Matt expressing bewilderment at Scottie's choice of t-shirts. One of which simply features the words "Mrs Clooney".
Creator Cameo: The original author of the book Kaui Hart Hemmings plays Matt's secretary.
George Clooney garnered arguably the most praise of his career for playing a character who is neither the slyest or most intelligent man in the room, but just a stressed-out father dealing with his dying wife and estranged children. Clooney took the part precisely for this reason.
Similarly, Matthew Lillard proved he can play a straight, dramatic role against an A-lister and got a Career Resurrection out of it.
Judy Greer, usually known for her comedic roles, gives a suprisingly understated and powerful performance.