Arliss copes with the sudden death of a close friend who was the same age. The sobering news sends the workaholic on a road trip of self-discovery into the Nevada desert, where he meets a mysterious prospector (John Rhys-Davies). Also, Kirby lines up a client who makes liquor-filled chocolates. Major League pitcher Curt Schilling has a cameo.
An old friend of Rita's steals more than Arliss's heart; Stanley and Kirby try to cook up an endorsement deal with boxer Roy Jones Jr. Ned: Joe Bologna. Penny: Diane Farr. Mrs. Jones: Marla Gibbs. Rita: Sandra Oh. Arliss: Robert Wuhl.
Arliss and Stanley try to persuade a former chess king to get back in the game; an old flame (James Madio) returns to woo Rita. Bobby: John Glover. Igor: Reuven Bar. Lenore: Eileen Brennan. The NBA's Mike Bibby has a cameo.
A football reporter who works on the sidelines (Lisa Long) spars with network execs who think she's too old for the job; Stanley's highly recruited nephew chooses a big-time college-football program. Cecil: Keith David. Jordan: Sharif Atkins. Cameos include Jim Mora, Van Earl Wright and Doug Krikorian.
Arliss and Kirby help a former client bent on a career in politics; Rita looks for a spokesmodel for a new line of clothing. Eli: David Ogden Stiers. Ken: Glenn Frey. Cameos include Bill Romanowski, Jeremy Roenick, Tyrone Wheatley, Reggie Miller, Luis Gonzalez.
Arliss winds up in an unintended destination after a trip down memory lane with an old acquaintance (Seymour Cassel); Kirby's fling with a female bodybuilder (Carla Haug) ends in disaster. Tyler: Rod Tate. Cameos include Steve Mariucci, Tony Gonzalez and Jack LaLanne.
Arliss goes to bat for charity while helping a major-league pitcher (Grant Show) through a difficult career move. Holland Pound: Robin Atkin Downes. Fred: Michael Trucco. Cameos include Billy Bean, Bruce Hornsby, Tara Lipinski, Quentin Richardson, Darius Miles and Maurice Greene.
Much to Kirby's chagrin, Arliss takes a new protégé under his wing; Rita likes what (or who) is cooking at Stanley's restaurant. Fabio, Kristoff St. John, John Reilly. Cameos include Kordell Stewart, Deion Sanders and Jillian Barberie. Rita: Sandra Oh. Kirby: Jim Turner.
Arliss crunches numbers to sign a superstitious NBA draft pick; Stanley shepherds a client's daughter's entrepreneurial streak. Cameos include Bill Goldberg, Pat Croce, Jason Giambi and Robert Shapiro. Stanley: Michael Boatman. Arliss: Robert Wuhl.
Arliss sets a screen for an NBA owner (Keith Carradine) with a wandering eye; Rita finds fault with a tennis pro's political interests; Stanley tries to find out who dented his new car. Cameos include Elton Brand and Ray Lewis. Meredith: Cynthia Sikes. Bobbie: Susan Egan. Ricky: Corey Pearson.