1999 • 22 episodes
Episodes
Episode 1 • Oct 05, 1999
Casey tries to find the courage to ask Dana out, Isaac's back at work, and Jeremy and Natalie have a fight.
Episode 2 • Oct 12, 1999
Dana goes to a bachelorette party and has an epiphany, Dan has breakfast with Hillary Clinton, and Isaac brings in a ratings guy.
Episode 3 • Oct 19, 1999
The staff are stressed out by Sam Donovan's presence, and things get worse when J.J. stops by to give them notes.
Episode 4 • Oct 26, 1999
Casey does everything he can to win the Sports Night “Who's Cooler: Dan or Casey?” internet poll. Dana has dinner with an old school friend.
Episode 5 • Nov 02, 1999
Jeremy readies the show's computer systems for Y2K. Dan meets a woman in a bar, discovering later that she's a psychologist.
Episode 6 • Dec 07, 1999
Casey wants to edit an interview to cast a ballplayer in a more favorable light, Dan has trouble taping a teaser, and The Vatican declares there's no such place as Hell.
Episode 7 • Dec 14, 1999
Jeremy has to fire an intern, and the team covers breaking news of a football steroid scandal.
Episode 8 • Dec 21, 1999
Dana's brother comes to visit. Natalie asks Dan to review her audition tape.
Episode 9 • Dec 28, 1999
It's a very slow news day, Casey goes on a date with a woman named Pixley, and Jeremy is up for an award.
Episode 10 • Jan 11, 2000
Dana begins to see the flaw in her dating plan. Dan wants to use Isaac in a feature on the 1951 New York Giants pennant win.
Episode 11 • Jan 18, 2000
Dan and Casey cover a boxing match. Dan's father visits.
Episode 12 • Jan 25, 2000
The show lands an interview with Michael Jordan but there are a few strings attached. Sam returns.
Episode 13 • Feb 01, 2000
Dan tries to get the night off for a Tom Waits concert. Dana inherits a gun.
Episode 14 • Feb 08, 2000
It's Sam's last day at the show, Jeremy and Natalie break up, and Casey gets his eyes examined.
Episode 15 • Feb 29, 2000
Natalie organizes a post-show trivia game but excludes Jeremy, who ends up meeting a woman at a bar.
Episode 16 • Mar 07, 2000
Dan reacts to not making the “100 Most Influential People in Sports” list. Dana goes to church.
Episode 17 • Mar 14, 2000
The team covers the first round of the NFL draft. Jeremy is nervous about Jenny's visit to the studio.
Episode 18 • Mar 21, 2000
It's the second round of the NFL draft. Jenny visits, and Dan and Casey fight.
Episode 19 • Mar 28, 2000
The network's cutting costs and jobs may be on the line. The staff sit for Passover Seder, and Dan hopes this will afford him the chance to mend a few fences.
Episode 20 • Apr 04, 2000
Natalie has a job interview with Saturday Night Live. Dan hires a publicist.
Episode 21 • May 09, 2000
Dana meets a man with inside information on the sale of the network. Dan and Casey have a job offer in Los Angeles.
Episode 22 • May 16, 2000
Rebecca returns, Natalie and Jeremy rekindle their relationship, and the network is sold.