A famous actor preparing to play Monk in a film about the events of the episode Mr. Monk and the Astronaut gets a little too close to one of Monk's real-life murder investigations. Guest stars Greg Grunberg, Peter Weller, and Stanley Tucci in an Emmy-award winning performance.

When a union boss's death threatens to prolong a city-wide garbage strike in San Francisco, it's up to Monk to help end the strike by determining whether the boss' death was suicide or murder. Guest stars Chi McBride, David DeLuise, and Alice Cooper.

Julie and her teammates hire Monk to look into the suspicious death of their basketball coach, a death in which they believe there may have been foul play.

Monk tries to solve the murder of a firefighter after losing his eyesight, and finds that it has connections to the fire that the rest of the ladder company had been responding to. Based on the novel Mr. Monk Goes to the Firehouse by Lee Goldberg.

When Natalie convinces Monk to go into business as a private eye, his first case is a seemingly innocuous fender bender that leads to a far more dangerous investigation. Guest stars Frederick Weller, Graham Beckel, Francesca Vannucci, and Sharon Lawrence in her first appearance as Linda Fusco.

Monk attends his college reunion and uncovers a complex murder plot against one of his former classmates that starts with the murder of a longtime nurse. Guest stars Cynthia Stevenson and Reginald VelJohnson.

When Dr. Kroger retires after his cleaning lady is killed, it's up to Monk to solve the case and get Kroger back to work. Guest stars Tim Bagley, Rick Curry, Cody McMains, and Gordon Clapp.

Monk and Natalie go to a rock concert to look for Captain Stottlemeyer's son Jared and find themselves investigating the murder of one of the roadies. Guest stars Brad Hunt andJon Kyle Hansen.

When Monk's truck driving father rolls into town at Christmas time, Monk joins him on the road, where they stumble across a very peculiar mystery. Guest stars Dan Hedaya, Brian Kerwin, and Emmy Clarke. Monk's second annual Christmas special.

A missing billionaire suffering from leprosy comes out of hiding to hire Monk, who soon finds himself in the midst of a shadowy murder plot worthy of a classic Hollywood film noir. The episode was broadcast in black & white as well as in color. Both black and white and color versions are included on the season 5 DVD. Guest stars Sarah Brown, Paul Blackthorne, and Emmy Clarke.

Fun-loving everyman Hal Tucker bumps into Monk, and the two become fast friends. For the first time in his life, Monk appears to have a buddy. But is Hal up to something? Guest stars Andy Richter.

When Natalie suspects foul play in the deaths of the Buchanans - her parent's wealthy neighbors, Monk goes undercover as a butler to investigate. Guest stars Sean Astin, Michael Cavanaugh, and Holland Taylor.

Monk goes toe to toe with a popular radio shock jock whom he suspects of killing his wife. There's only one problem: at the time of death, he had an airtight alibi - he was on the air. Guest stars Steven Weber, Jarrad Paul, Heather Tom, Danny Woodburn, Kevin P. Farley, and Melora Hardin.

When Lt. Disher inherits a farm from an uncle who committed suicide, he decides to quit the police force and start a new life in the country. But Disher soon suspects that his uncle was murdered, so Monk joins him on the farm to investigate. Guest stars Brooke Adams and Ricardo Chavira.

When the mysterious Six Way Killer strikes in San Francisco, Monk must match his detective skills against the flashy forensic technology of a federal agent as they both pursue the murderer. Guest stars Chris Williams and Emmy Clarke.

Monk goes to the emergency room for a bloody nose, but when a doctor in the hospital turns up dead, Monk joins the murder investigation, and soon his own life is in grave danger. Guest stars Charles Durning and Dan Butler.