Monk (2002-2009) followed the life of former detective Adrian Monk (Tony Shalhoub), an investigative genius living with obsessive-compulsive disorder and struggling to cope after the brutal murder of his wife, a premise that often resulted in heartbreaking episodes. With the support of his nurse and personal assistant Sharona, Adrian returns to work as a consultant for the San Francisco Police Department. Monk’s primary drive is to find who killed Trudy, and the circumstances he winds up in along the way are comedic and tragic in equal measure.

This fan-favorite police procedural takes a beautifully compassionate approach to mental illness, grief, and trauma, and does all of this without sacrificing comedic relief. While creator Andy Breckman manages to keep the show surprisingly lighthearted despite its heavy themes, some of Monk‘s best episodes are also the most heartbreaking. From devastating trauma and loss to heartwarming and wholesome friendships, Monk had some truly emotional moments.

10

Mr. Monk Befriends A Fellow Widower

Adrian Helps Samuel Waingaya Find Justice For His Wife

In season 5 episode 11, “Mr. Monk Makes A Friend,” Adrian is disturbed by a Nigerian flutist busking in the street outside his apartment. Upon being confronted about the “noise,” the man reveals he cannot leave the street corner because he is sitting a vigil for his wife, who was killed there 2 weeks prior. Adrian takes the gentleman back to his apartment, where he learns the man’s name is Samuel Waingaya (Adewale Akinnuoye-Agbaje). When he discovers Samuel’s wife’s death was no mere accident, Monk promptly steps in and solves the case.

Monk: “What’s it like?”

Samuel: “What is what like?”

Monk: “Knowing.”

Samuel: “Knowing is everything.”

Soon after their introduction, Adrian shared with Samuel that his own wife, Trudy, was also murdered. The two immediately bonded over their shared grief, with Samuel reaching out to lay a consoling hand on Mr. Monk’s shoulder. He became an unlikely friend to Mr. Monk, empathizing with his loss and encouraging Adrian not to give up on his mission to solve Trudy’s murder. Their dynamic was tragic, but wholesome and supportive in a way Monk desperately needed, and a return of their friendship in a Mr. Monk’s Last Case sequel would be heartwarming.

9

Mr. Monk Sees His Wife In A Stranger’s Eyes

Mr. Monk Meets The Woman Who Received Trudy’s Cornea Transplant

In season 6 episode 9, “Mr. Monk Is Up All Night,” Mr. Monk bumps into a woman on the street and finds that he cannot stop thinking about her. This obsession causes him days of insomnia, leading him to wander the streets of San Francisco late at night looking for this strange woman. In the process, he witnesses what appears to be a drug deal gone wrong, resulting in the murder of a cop. It is later discovered that the crime was staged to extort money from one of the apparent witnesses.

Unfortunately, the premise of this episode is a factual error, as a corneal transplant would not cure the disease Maria claimed to have (retinitis pigmentosa, which does not affect the corneas, but instead the retinas). More importantly, this procedure does not affect the iris, so Adrian would not have been able to recognize Trudy’s eyes in the recipient of her corneas.

As the suspects are apprehended, another odd coincidence reunites Monk with the woman from the street, as she happened to have been Stottlemeyer’s (Ted Levine) cab driver that evening. When Monk sees her a second time, he notices that she has a tattoo of the same date his wife died, and it is revealed that Maria (Terri Hoyos) was the recipient of a cornea transplant from Trudy. The grief is palpable as Monk realizes that part of his wife lives on in this complete stranger.

8

Mr. Monk Tries A Medication For OCD

A Prescription Completely Changes Mr. Monk’s Personality

In season 3 episode 9, “Mr. Monk Takes His Medicine,” Dr. Kroger encourages a depressed Monk to try an experimental medication for obsessive-compulsive disorder, but the side effects prove to outweigh the benefits. The new prescription causes Monk to lose his brilliant investigative abilities due to inattention and radically alters his personality.

The alleviation of Adrian’s obsessive compulsions leads him to become friendly and fearless but also loud and obnoxious. Monk’s friends and coworkers express concern over his changed behavior, but this only causes him to feel defensive, accusing them of not wanting him to be happy or healthy. While this episode has strong comedic elements, it is ultimately one of the most tragic episodes of the show, exploring the depths of Monk’s struggles with his mental health and the depression that is so often created by relentless anxiety and compulsions.

7

Mr. Monk Reconciles With His Brother, Ambrose

Adrian Finds Out Why Ambrose Disappeared For 7 Years

In season 2 episode 11, “Mr. Monk and the Three Pies,” Mr. Monk reunites with his estranged brother, Ambrose (John Turturro). When his neighbor’s wife disappears under mysterious circumstances, Ambrose contacts his brother for help, but Adrian is initially hesitant to investigate. Their relationship is strained at best after his brother’s 7-year absence from his life following the death of Trudy. Monk soon solves the case, but their conflict comes to a head when Ambrose invites Adrian to stay for dinner and sets a third place for their father, who abandoned their family many decades prior.

Ambrose adopts one of Adrian’s most well-known catchphrases in this episode: “It’s a gift and a curse.”

Angered by the naive hope that their father will one day return and feeling abandoned by Ambrose, Adrian rounds on his brother when he says he loves him. Ambrose breaks down, confessing to Adrian that the reason he had stopped calling was because he blamed himself for Trudy’s death. Unbeknownst to Adrian, Trudy had been in the parking garage that day because Ambrose, who lives with agoraphobia, had asked her to pick up cough syrup for him when he was sick. Touchingly, Monk hugs his brother as he reassures Ambrose that Trudy’s murder was never his fault.

6

Mr. Monk Reconciles With His Father, Jack

Adrian Processes His Father Having Abandoned Him 40 Years Earlier

In season 5 episode 9, “Mr. Monk Meets His Dad,” Monk’s childhood trauma comes to light when his father, Jack Monk, reappears in his life after having abandoned their family 40 years prior. His father is now working as a truck driver and, after being arrested for running a red light, takes advantage of his connection to Adrian to get bailed out. Jack then takes Adrian on the road with him over Christmas, giving the two a chance to hash out their longstanding family feud.

Although Jack eventually makes a heartfelt apology for the damage he did, he also issues numerous excuses for the abandonment of his two sons. Adrian’s obsessive-compulsive disorder predated his father leaving, but this abandonment wound is pervasive in Adrian’s life and is only exacerbated by further traumatic events (such as Trudy and Dr. Kroger’s deaths, as well as Monk’s eventual loss of both his assistants). However, the end scene of this episode is particularly heartwarming, as Jack makes amends by finally teaching Adrian how to ride a bike.

5

Mr. Monk Finds A Friend

A Con-Artist Takes Advantage Of Monk’s Need For A Friend

In season 5 episode 11, “Mr. Monk Makes a Friend,” Mr. Monk accidentally bumps into a man outside the grocery store and the two become fast friends. Hal (Andy Richter) seems to love Adrian and wants to hang out with Monk 24/7.

This newfound friend even asks to tag along to crime scenes, and his apparent obsession with Adrian raises the eyebrows of Stottlemeyer and Natalie alike. Although concerned for the sweet and gullible Mr. Monk, they back off from expressing suspicion about Hal’s motives when Monk becomes defensive, admitting he has never had a friend before.

4

A Radio DJ Mocks Trudy’s Death

Disrespect Of His Late Wife Is Where Adrian Draws The Line

In season 5 episode 13, “Mr. Monk is On the Air,” Monk is devastated by an insufferable radio DJ’s disgusting jokes about Trudy’s murder. Shock jock Max Hudson (Steven Weber) had planned his wife’s murder, training his dog to respond to the catchphrase, “Jiggle me timbers!” When he spoke these words on air, the dog had been conditioned to turn on the gas at the fireplace and close the bedroom door behind himself, creating the perfect alibi for Hudson. In a recklessly arrogant move, Hudson then invited Monk onto his show twice, knowing he was investigating his late wife’s death.

Following some painfully un-funny jokes from Mr. Monk, Hudson began to mock Trudy’s murder, making jokes so insensitive that even his equally obnoxious co-hosts balked. His sickening comments pushed Mr. Monk over the edge, leading him to attack Hudson on air. While Mr. Monk is frequently the butt of the joke throughout the show, this scene is hands down the most horrific and infuriating instance – although some comedic relief is arguably provided by Adrian preparing for his airborne attack by taking off his headphones as if they were earrings.

3

Mr. Monk Finally Solves Trudy’s Case

Mr. Monk Finds Justice For Trudy And Gains A Daughter

In season 8 episode 16, “Mr. Monk and the End,” Mr. Monk finally solves the murder of his beloved wife, Trudy. From start to finish, this two-part series finale is one of the best episodes of Monk, and certainly one of the most satisfying arcs. That being said, it has several heartbreaking moments even beyond witnessing Monk’s grief as he finally discovers who killed Trudy.

Leland Stottlemeyer: “You know, I always thought that Monk was not all there. Like there was something missing, like he was less than human. But he wasn’t missing anything. He was seeing more than anybody, he was feeling more than anybody. Hell, that’s his problem. He was too human. If we had more like him, we’d be better off.”

In the series finale, Monk has been exposed to an unknown synthetic toxin and has been given only a few days to live. Watching the people who love him come to terms with his imminent demise is heartbreaking. Natalie in particular struggles with the news, breaking down into tears as Monk starts to accept he is running out of time.

The very last lines of the final episode pay homage to the very first lines of the pilot episode, in which Monk pauses mid-investigation to wonder aloud if he left the stove on. This is referenced again in the opening dialogue of the movie sequel, Mr. Monk’s Last Case: A Monk Movie.

Most notable, however, is the scene in which Adrian meets Trudy’s daughter Molly for the first time, and cannot stop hugging her. The two immediately develop a close bond, with Mr. Monk following her everywhere. Molly is later recast for Mr. Monk’s Last Case: A Monk Movie.

2

Mr. Monk Adopts A Dog

Mr. Monk Needs Family And Finds It In A Sheepdog

In season 8 episode 11, “Mr. Monk and the Dog,” Mr. Monk temporarily adopts a sheepdog named Shelby, who formerly belonged to a murder victim. When the dog first approaches him and licks his hand, Adrian is horrified by the thought of taking her home, but caves when it comes to light that Shelby would be euthanized if no one wanted her. Throughout the investigation, Monk forms a strong bond with this furry friend, bringing her ice cream and even managing to pet her with his gloves off.

Throughout the show, Mr. Monk shows a great deal of empathy for others like him – widows and widowers, children, and animals alike. This particular bond is more poignant than usual, however, as the episode starts off with Adrian attending Natalie’s (Traylor Howard) 25th annual family reunion, an event that brings his loneliness and lack of a family into stark relief. Shelby becomes his family for a short time, and this theme is brought back by another dog friend Mr. Monk’s Last Case: A Monk Movie.

1

Mr. Monk Adopts A Kid

Adrian Learns About Unconditional Love (Again)

In season 3 episode 16, “Mr. Monk and the Kid,” Mr. Monk meets a toddler named Tommy Grazer (Preston & Trevor Shores) who is involved in a missing persons case. Tommy had stumbled across the missing man’s severed finger while playing in the park and, upon the arrival of the police, quickly took a shine to Mr. Monk. When it became apparent that the young boy was to be removed from his foster home, Adrian took on legal guardianship of Tommy, who seemed to share many of Monk’s eccentric behaviors.

Monk: “And then the most wonderful and surprising thing of all happened: Mr. Monk discovered that he loved that Little Prince. But he also realized the Little Prince could never live happily ever after if he stayed at Mr. Monk’s house…because Mr. Monk can barely take care of himself. So…they’re gonna have to say goodbye.”

Monk quickly blossomed into a loving and involved father figure but gradually came to realize that fostering Tommy was not in the child’s best interest. With prolonged exposure to Mr. Monk, the boy’s compulsions seemed to intensify. As such, Adrian became terrified of potentially hurting Tommy’s mental health.

The season 3 finale is one of only 2 episodes to feature a different version of the Monk theme song by Jeff Beal. (This track usually plays during the end credits, even after the original theme was replaced by Randy Newman’s “It’s a Jungle Out There” in season 2). The orchestration of this end credits sequence features the upper register of a piano rather than a classical guitar and upright bass, and the theme is slowed down significantly for a more poignant feel. It is entitled Tommy’s Theme, and is also heard in season 4 episode 2, “Mr. Monk Goes Home Again.”

The storytime version of the iconic Monk “here’s what happened” spiel is arguably the most tragic non-Trudy-centric scene in the show, with Adrian expressing love for his adopted son as he simultaneously acknowledges the necessity of letting him go. On Natalie and Dr. Kroger’s advice, Adrian makes the heartbreaking decision to surrender Tommy to another foster family.