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22 Episodes 1999 - 2000
Episode 1
Tue, Oct 5, 1999 30 mins
Dan goads Casey to ask Dana out, given that the 90-day mourning period for breakups has expired. Meanwhile, Natalie and Jeremy try to work things out after she gets a lucrative job offer; and Isaac hits a stumbling block on his road to recovery...and job stability. Isaac: Robert Guillaume. Kim: Kayla Blake. Will: Ron Ostrow.
Episode 2
Tue, Oct 12, 1999 30 mins
While awaiting the arrival of a ratings expert (William H. Macy), Dana drops a bombshell on Casey about their first date. Meanwhile, Dan falls apart over the fact that he misspoke in front of the First Lady. Dana: Felicity Huffman. Dan: Josh Charles. Kim: Kayla Blake.
Episode 3
Tue, Oct 19, 1999 30 mins
Staff-wide scorn for Sam (William H. Macy) leads to a lifeless show, bringing unwelcome attention from a team of job-killing network bigwigs. But as the higher-ups begin to chop the dead wood, Sam steps up to save some hides. J.J.: Robert Mailhouse. Isaac: Robert Guillaume. Dan: Josh Charles. Casey: Peter Krause. Natalie: Sabrina Lloyd.
Episode 4
Tue, Oct 26, 1999 30 mins
In a letter to Jeremy's sister, Natalie recounts Dana's clothing-optional dinner date and how Casey rigged the CSC Internet poll in his favor. Meanwhile, Isaac asks Sam to drop the facade and join the team. Sam: William H. Macy. Kim: Kayla Blake. Jeremy: Josh Malina. Dan: Josh Charles.
Episode 5
Tue, Nov 2, 1999 30 mins
Jeremy scrambles to save the show---and face---after his faulty Y2K test kills the studio's juice hours before airtime. Meanwhile, Dan picks up a therapist at a bar, but has no idea if he's made a date or an appointment with the woman. Abby: Jayne Brook. Will: Ron Ostrow. Chris: Timothy Davis-Reed. Dana: Felicity Huffman.
Episode 6
Tue, Dec 7, 1999 30 mins
Casey battles Dana for editorial control after his favorite baseball player (Richard Steinmetz) rails against New York during their taped interview. Meanwhile, Abby (Jayne Brook) gets in Danny's face about his need to confront a personal demon that's throwing off his performance on the show. Kim: Kayla Blake. Danny: Josh Charles. Dana: Felicity Huffman. Isaac: Robert Guillaume.
Episode 7
Tue, Dec 14, 1999 30 mins
Dan's therapist (Jayne Brook) tries to get to the bottom of his obsessive flirting. Meanwhile, Natalie pressures a reluctant Jeremy to fire an incompetent staff member (Charlie Finn), while Casey investigates a drug scandal involving a professional football team. Casey: Peter Krause. Natalie: Sabrina Lloyd. Dana: Felicity Huffman. Dan: Josh Charles. Jeremy: Joshua Malina.
Episode 8
Tue, Dec 21, 1999 30 mins
As Secret Santa woes plague the staff, Dana awaits the arrival of her linebacker brother (Eric Bruskotter) after he's busted for steroids. Meanwhile, Dan feeds Natalie a line after screening her audition tape for an anchor slot. Dana: Felicity Huffman. Jeremy: Joshua Malina. Kim: Kayla Blake. Elliot: Greg Baker.
Episode 9
Tue, Dec 28, 1999 30 mins
As per Dana's "plan," Casey agrees to a date with another woman (Megan Ward), who takes issue with his reason for asking her out. Back at CSC, the staff scrambles to fill an hour on a very light news day; and Jeremy plans his acceptance speech for an award he hasn't won. Elliot: Greg Baker. Waiter: Darren Foreman. Natalie: Sabrina Lloyd. Casey: Peter Krause.
Episode 10
Tue, Jan 11, 2000 30 mins
Isaac refuses to help Dan report on a classic baseball game which he attended, while Casey (Peter Krause) takes a swing at another date with Pixley (Megan Ward). Jack: Darren Foreman. Mike: James Edson. Howard: Tom Cavanagh.
Episode 11
Tue, Jan 18, 2000 30 mins
While prepping to cover a major fight, Dana and Casey duke it out over their stalled fling, and Dan's dad (Peter Riegert) hits town for a tense visit. But after the match goes south, the CSC staff bands together to knock out a killer show. Cut Man: Allen Garfield. Mike: James Edson. Natalia: Sabrina Lloyd. Dana: Felicity Huffman.
Episode 12
Tue, Jan 25, 2000 30 mins
Sam (William H. Macy) steps in when the guys get stuck interviewing a hoops star who only wants to pitch his new cologne on their show. Meanwhile, Sally spills her torrid past to the wizened ratings expert, who has no idea---or interest in---what she's talking about. Sally: Brenda Strong. Dave: Jeff Mooring. Casey: Peter Krause. Dana: Felicity Huffman.
Episode 13
Tue, Feb 1, 2000 30 mins
Dan scores a night off, leaving Casey saddled with a morbid co-anchor; Sam (William H. Macy) gives Dana a lesson in gun care; and Natalie tries to talk Jeremy into hitting the New York club scene. Steve: Cress Williams. Dave: Jeff Mooring. Will: Ron Ostrow.
Episode 14
Tue, Feb 8, 2000 30 mins
While Casey tries to write the show with blurred vision, Dana sets her sights on finding out what caused an office breakup. In the meantime, Sam's days at CSC come to a close; and the show is roped into the investigation of a riot at the Garden. Dana: Felicity Huffman. Sam: William H. Macy. Peter Sadler: Spencer Garrett.
Episode 15
Tue, Feb 29, 2000 30 mins
While the staff plays a celebrity-name game at the studio, Jeremy meets a stranger (Paula Marshall) with some star power of her own. Meanwhile, one of the anchors makes a magazine's list of sports authorities and must break it to his cohort. Will: Dave Ostrow. Dave: Jeff Mooring. Casey: Peter Krause. Dana: Felicity Huffman.
Episode 16
Tue, Mar 7, 2000 30 mins
During a session with his therapist (Jayne Brook), Dan recounts the victory---and defeat---of an aging track star, and Jeremy's porn-star crush. Meanwhile, Dana has a religious experience while sitting out a rain storm. Jenny: Paula Marshall. Oscar: Derek Webster. Jack: Darren Foreman. Dave: Jeff Mooring.
Episode 17
Tue, Mar 14, 2000 30 mins
Part 1 of two. Amid CSC's football-draft coverage, Jeremy scrambles to hide Jenny's day job from Natalie (Sabrina Lloyd), who goes out of her way to let the staff know that she is now available. Meanwhile, the anchors face off over Casey's recent rise in popularity. Will: Ron Ostrow. Dana: Felicity Huffman. Karen: Susan Leslie. Jack: Darren Foreman.
Episode 18
Tue, Mar 21, 2000 30 mins
Conclusion. Deep into CSC's football draft show, Casey (Peter Krause) spills the beans about his role in Dan's career at the network, causing an on-air situation that could leave an empty seat at the Sports Night desk. Meanwhile, Jeremy loses his cool when Dana and Nat meet his porn-star girlfriend. Jenny: Paula Marshall. Kelly: Amy Powell. Aaron: John Kidd. Elliot: Greg Baker.
Episode 19
Tue, Mar 28, 2000 30 mins
Dana and Isaac learn that the network is cutting back funding for the show and that Natalie's job may be lost. Meanwhile, Jeremy and Dan plan a mid-day seder at the station. Mitchel: Tim Dekay. Stans: John de Lancie. Dana: Felicity Huffman. Jeremy: Josh Malina. Dan: Josh Charles.
Episode 20
Tue, Apr 4, 2000 30 mins
Amid rumblings of internal layoffs, Jeremy and Casey look into the network's stock---and find a shocking truth about their job security. Meanwhile, Natalie (Sabrina Lloyd) eyes another job on a late-night sketch show. Catherine: Alanna Ubech. Jeremy: Joshua Molina. Casey: Peter Krause.
Episode 21
Tue, May 9, 2000 30 mins
The gang gathers at Anthony's to mull over the future of the show, where a stranger piques Dana's interest with inside information about the bidding for Continental Corp. Stranger: Clark Gregg. Will: Ron Ostrow. Dana: Felicity Huffman. Dan: Josh Charles. Casey: Peter Krause.
Episode 22
Tue, May 16, 2000 30 mins
In the second-season ender, a mystery man (Clark Gregg) gives Dana the sad scoop on CSC's fate after the network is bought out by an upstart company with no need for a cable channel. Meanwhile, Casey prepares to look for new work without Dan, who is reunited with a familiar face from his past. Rebecca: Teri Polo. Kim: Kayla Blake. Elliot: Greg Baker.