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- Season 5 overviewSep 23, 1998-May 4, 199922 episodesSeason 5 episodes1. Bill Moves On Sep 23, 1998
- The WNYX staff deals with the sudden death of colleague Bill McNeal; guest Khandi Alexander.
- 2. Meet the Max Louis Oct 7, 1998
- Dave decides to hire Bill's old friend Max Louis (Jon Lovitz) as on-air talent.
- 3. Lucky Burger Oct 14, 1998
- Matthew hires Joe to research Max's radio history for damaging information.
- 4. Noise Oct 21, 1998
- Joe makes a relaxation tool for Dave; Lisa questions Max about segments he made.
- 5. Flowers for Matthew Oct 28, 1998
- Joe uses Matthew in an experiment; Max wonders if Beth is interested in him.
- 6. Jail Nov 4, 1998
- A business rival takes control of WNYX when the FBI puts Jimmy in jail.
- 7. The Lam Nov 11, 1998
- When Jimmy breaks out of jail, Matthew hunts for him; Lisa dates Johnny.
- 8. Clash of the Titans Nov 24, 1998
- Jimmy's confession shocks staffers when they attend his trial; guest Adam West.
- 9. Boston Dec 9, 1998
- Dave's former teacher asks him to make a videotape for his alma mater.
- 10. Spooky Rapping Crypt Dec 15, 1998
- Beth and Jimmy have the same idea; Matthew believes he's being manipulated.
- 11. Stinkbutt Jan 5, 1999
- Jimmy hires a security adviser (Toby Huss); Lisa and Matthew wear the same shirt.
- 12. Apartment Jan 12, 1999
- Dave and Lisa vie for the same coveted apartment; Joe creates WNYX website.
- 13. Towers Feb 2, 1999
- On his 30th birthday, Matthew changes his appearance and demeanor.
- 14. Hair Feb 9, 1999
- Jimmy revisits the 1960s when Joe hypnotizes him to resolve a past experience.
- 15. Assistant Feb 16, 1999
- Lisa's new assistant (Tiffani-Amber Thiessen) ignores her work, tuning in to Dave.
- 16. Wino Feb 23, 1999
- Matthew finds Jimmy's nemesis Johnny (Patrick Warburton) living as a bum.
- 17. Wedding Mar 2, 1999
- Dave discourages Lisa who prepares for her wedding to homeless Johnny.
- 18. Ploy Mar 9, 1999
- In a ploy to get Beth to date him, Max announces he's leaving WNYX.
- 19. Padded Suit Apr 13, 1999
- Dave makes WNYX staffers adhere to job descriptions to improve professionalism.
- 20. Freaky Friday Apr 20, 1999
- Matthew loses Jimmy's fortune in a computer snafu when the two swap lives for a day.
- 21. Retirement Apr 27, 1999
- Staff plans a farewell party when Jimmy James announces his retirement.
- 22. New Hampshire May 4, 1999
- All except Matthew and Dave leave to work at Jimmy's rural radio station.