Mr. Monk's 100th Case
Encyclopedia
"Mr. Monk's 100th Case" is the seventh episode of the seventh season
of the USA Network
TV series Monk
, and, true to its name, it is the 100th episode overall. Purporting to be a retrospective of Adrian Monk
's career, it reunites several actors who previously appeared on the show.
). He explains that on tonight's broadcast of In Focus, viewers will be following Adrian Monk
, a modern day Sherlock Holmes
and consultant for the San Francisco Police Department
, as he attempts a career milestone: solving his 100th case. This 100th case involves a serial killer
who murders young women and then steals their lipstick. Can Monk find the killer before he strikes again?
The scene changes to a viewing party at Novak's house, which includes Monk, Natalie Teeger
, Captain Leland Stottlemeyer
, Lieutenant Randy Disher, and some of their police officers.
The episode is interspersed with a biography of Monk, and interspersed with interviews of people close to Adrian. These include various colleagues like Natalie, Stottlemeyer and Disher, acquaintances like Marci Maven and Adrian's elder brother, and even some of the criminals Adrian has brought to justice over the years, such as Hal Tucker and Jimmy Belmont. It also touches on his lingering obsession with solving Trudy's murder. A running gag throughout the episode is how at each commercial break, Stottlemeyer changes the channel to a basketball game to check the score.
The documentary starts around July 18, when actress Cassandre Rank is found strangled to death in a building lobby. It seems like an interrupted robbery - the police believe that the victim was checking her mail when the killer broke a pane on the door, reached in and opened it, then killed the luckless actress with a rope. After having a few light bulbs fixed on a chandelier, Monk notices an interesting clue: there are glass shards from the door pane on top of the body, but there are none underneath. Also, even though there are traces of Cassandre's lipstick on her coffee cup and on her lips, there is no lipstick in her purse. He concludes that the victim knew the killer, meaning that this was no random attack. He believes that the victim was checking her mail when she saw the killer through the door. She let him in because she wasn't threatened by him and he was someone she knew, which was a big mistake - he killed her, stole her lipstick, and then punched through the door to make it look like a break-in. (In an inserted interview, Stottlemeyer mentions that he didn't tell the press about the missing lipstick; he notes that he does this on major cases because if they do get a confession later on, they'll have an easier time verifying that said confession is genuine.)
The police have no possible leads and no suspects. At this point in time, no one knows that Cassandre's killer will strike again: A few days later, however, another actress, Barbara McFarland, is strangled to death at her apartment. Examining the scene, Monk finds all the same clues, including the missing lipstick and lack of forced entry, that suggest that Cassandre Rank's killer is still at large. Victim #2, like Victim #1, was a part-time actress and waitress.
Monk and Natalie travel to a vampire-themed restaurant that both women had worked at to check out a possible lead. They ask the manager (who keeps slipping in and out of his character as a vampire throughout the interview) for his employment records. However, this lead turns out to be a dead end, as when they receive the employment records, they find that the victims didn't work at the place at the same time.
This isn't the last of it, however: a few days later, victim #3, Miranda Terhume, is strangled to death near her car at a parking lot in Daly City. Once again, all of the clues are the same as those at the first two crime scenes. As she didn't work at the restaurant that Cassandre Rank and Barbara McFarland worked at, that lead has now been declared a false lead.
After several days without a break, Monk makes a keen observation: All three victims of the so-called Lipstick Killer (the name chosen for the man, based on his M.O) had posed for Douglas Thurman, who owns a local photography studio. (In an inserted interview, Monk and Natalie mention that there were 50 cops in that room and they didn't spot the link, and Natalie notes that those cops could have been locked in the room for a year and not noticed the link, though Monk points out to her that he was standing next to the board.) The police bring Thurman in for questioning. As Stottlemeyer and Disher talk to him, he denies everything, although they point out the overwhelming amount of evidence against him.
With insufficient evidence to detain Thurman, they are forced to release him. Things take a startling twist that afternoon - Thurman disappears completely, failing to show up for a polygraph test. A statewide all points bulletin
is issued on Thurman, and meanwhile, a judge issues a search warrant
allowing the police to search Thurman's studio. The next morning, a SWAT
team raids Thurman's studio and apartment, and they find a rather beautiful incrimination in the studio - an eerie shrine to all three victims, with each woman's portrait having her respective lipstick smeared on it. They determine that they have their man, but Thurman himself has fled (in an interview, Disher admits that this was the low point of the investigation, as they had Thurman in handcuffs just the day before. Stottlemeyer notes that they should have never let Thurman go, but the law is the law - you can't detain someone unless you have enough evidence to suspect probable cause).
Later that same day, Kate Kindel, another model/actress, is found strangled to death at her house, and her lipstick has been taken. All of the clues are the same, suggesting Thurman might not be finished. As Monk looks around, he asks to have a light switch turned on and Novak switches on a lamp next to him. Just then, Stottlemeyer gets a call and learns that Thurman has been spotted in San Racine, in Southern California
, 300 miles south of San Francisco, hiding in a cheap motel
room. As a SWAT team moves in, Thurman chooses to shoot himself
rather than be captured. Monk has closed his 100th case, and the episode of “In Focus" wraps up to a round of applause from those at the viewing party.
During the viewing party, however, Monk is becoming a bit doubtful of himself, and is having second thoughts. After the documentary ends, Monk mentions a few oddities about Kate Kindel's death that cast doubt on Thurman being involved there: for one thing, when Thurman killed himself, he had Mexican currency in his pockets, meaning that he was fleeing south, towards Mexico
, but Kate Kindel was killed 50 miles north of San Francisco. Why would he go that far out of the way to commit a fourth murder, when he knew that the police were after him? Also, Monk remembers that Kindel was strangled from behind while the other victims were strangled from in front.
At Monk's insistence, they rewind the recording of the documentary back to when the SWAT team raids Thurman's studio. Monk notices a crucial detail: when comparing the "before" and "after" shots as the camera moves back and forth across the studio, he spots an additional roll of film in the "after" shot, standing up on the table. The roll is not in the "before" shot, meaning that the roll had been planted. This roll, Disher remembers, was the roll on which the pictures of Kate Kindel were found. Stottlemeyer points out that the SWAT team did not plant the additional roll, as every man on that team is a righteous guy, though Monk notes that there were other people accompanying the SWAT team on the raid.
Then, Monk asks to fast forward to a scene in Kate Kindel’s apartment, in a scene where he asks for someone to turn on the lights. Novak turns on the lamp next to Monk, but suspiciously, in the scene, he knows exactly which switch turns on that specific lamp. Monk concludes that Novak had been in Kindel’s apartment before the investigation.
Earlier in the episode, there have been repeat signs that there is trouble in paradise: Novak flirts shamelessly with several of the women at the party, including Randy's new girlfriend Jillian, an aspiring actress who specializes in being murdered on camera (Randy mentions that she was once bludgeoned to death on Dateline NBC
, and she also appears in the re-enactment scene of Kate Kindel's murder in the show). When he has her in a corner, Jillian acts embarrassed over a gaffe she has made, and Novak soothes her that everyone makes mistakes - his, he confides, was his wife, Melissa.
and the missing lipstick. As a result, it wasn't hard for Novak to frame Thurman for a fourth victim.
Novak knew that the opportunity to frame Thurman for Kindel's murder was the same morning that the police raided Thurman's studio. The night before, he went to Kindel's apartment and had her pose for some photographs. Because Thurman only used film photography, Novak had to use a camera that utilized film. After he took photos of Kindel, Novak killed her, and then staged the scene. He took her lipstick, because that was what Douglas Thurman would have done. The next morning, Novak accompanied the police as they raided Thurman's studio, and he set the roll of film down amongst the other film canisters (the tracking shot itself helped hide him planting the roll, and he was probably aware that as the shot was very quick and brief, no one would notice the extra canister). Kindel would now look like just another rather unfortunate victim of the homicidal photographer.
Novak says there is no proof, but then his estranged wife Melissa produces a lipstick that she found in his pockets on the night of the murder, and demands that the police check it for Kindel's DNA
. As Melissa hands the lipstick to Randy, Novak pulls out a gun and orders him to hand it over. Randy, exchanging a glance with Stottlemeyer, tosses the lipstick, distracting Novak for the second Stottlemeyer neads to sneak beside him, grab the gun, and deck Novak with a punch. The gun goes off, and Jillian crumples to the floor, clutching her side. Randy panics and yells for an ambulance, but then Jillian realizes that she's untouched, and apologizes, as this is a "force of habit". Randy compliments her on her performance, and the two kiss lovingly - leaving the rest of the company baffled. Novak is subsequently taken away.
The next morning, at Monk's apartment, Natalie reads a front page article about Novak's arrest. Monk, reflecting that one hundred cases is a nice, even number, considers retiring from his detective work. Natalie quickly figures that Monk is not thinking straight, and prepares to whack him with the newspaper. Then she realizes - when Monk caught Douglas Thurman, that was his 100th case. The arrest of James Novak, although related to Thurman and his murders, is a completely different case. Hence, Monk has in fact solved 101 cases. Natalie smugly tells Monk that if he wants to retire, he must solve another 99 cases (200) overall, and they start looking through the paper to see who has been killed over the past day.
Monk (season 7)
The seventh season of Monk originally aired in the United States on USA Network from July 18, 2008 to February 20, 2009. It consisted of 16 episodes. Tony Shalhoub, Traylor Howard, Ted Levine, and Jason Gray-Stanford reprised their roles as the main characters. A DVD of the season was released...
of the USA Network
USA Network
USA Network is an American cable television channel launched in 1971. Once a minor player in basic cable, the network has steadily gained popularity because of breakout hits like Monk, Psych, Burn Notice, Royal Pains, Covert Affairs, White Collar, Monday Night RAW, Suits, and reruns of the various...
TV series Monk
Monk (TV series)
Monk is an American comedy-drama detective mystery television series created by Andy Breckman and starring Tony Shalhoub as the titular character, Adrian Monk. It originally ran from 2002 to 2009 and is primarily a mystery series, although it has dark and comic touches.The series debuted on July...
, and, true to its name, it is the 100th episode overall. Purporting to be a retrospective of Adrian Monk
Adrian Monk
Adrian Monk is a fictional character portrayed by Tony Shalhoub and the protagonist of the USA Network television series Monk. He is a renowned former homicide detective for the San Francisco Police Department...
's career, it reunites several actors who previously appeared on the show.
Plot Synopsis
The episode opens in the form of the introduction to an "In Focus" documentary, hosted by James Novak (Eric McCormackEric McCormack
Eric James McCormack is a Canadian American actor, musician, writer and producer. Born in Toronto, he began his acting career performing in school plays at Stephen Leacock Collegiate Institute High School...
). He explains that on tonight's broadcast of In Focus, viewers will be following Adrian Monk
Adrian Monk
Adrian Monk is a fictional character portrayed by Tony Shalhoub and the protagonist of the USA Network television series Monk. He is a renowned former homicide detective for the San Francisco Police Department...
, a modern day Sherlock Holmes
Sherlock Holmes
Sherlock Holmes is a fictional detective created by Scottish author and physician Sir Arthur Conan Doyle. The fantastic London-based "consulting detective", Holmes is famous for his astute logical reasoning, his ability to take almost any disguise, and his use of forensic science skills to solve...
and consultant for the San Francisco Police Department
San Francisco Police Department
The San Francisco Police Department, also known as the SFPD and San Francisco Department Of Police, is the police department of the City and County of San Francisco, California...
, as he attempts a career milestone: solving his 100th case. This 100th case involves a serial killer
Serial killer
A serial killer, as typically defined, is an individual who has murdered three or more people over a period of more than a month, with down time between the murders, and whose motivation for killing is usually based on psychological gratification...
who murders young women and then steals their lipstick. Can Monk find the killer before he strikes again?
The scene changes to a viewing party at Novak's house, which includes Monk, Natalie Teeger
Natalie Teeger
Natalie J. Teeger is a fictional character on the American crime drama Monk. She becomes Adrian Monk's personal assistant midway through the third season of the show...
, Captain Leland Stottlemeyer
Leland Stottlemeyer
Captain Leland Francis Stottlemeyer is a fictional police officer played by Ted Levine on the American crime drama Monk. He is Captain of the San Francisco Police Department 's Homicide Detail, and a longtime friend of Adrian Monk from their days on the force together where he served as Monk's...
, Lieutenant Randy Disher, and some of their police officers.
The episode is interspersed with a biography of Monk, and interspersed with interviews of people close to Adrian. These include various colleagues like Natalie, Stottlemeyer and Disher, acquaintances like Marci Maven and Adrian's elder brother, and even some of the criminals Adrian has brought to justice over the years, such as Hal Tucker and Jimmy Belmont. It also touches on his lingering obsession with solving Trudy's murder. A running gag throughout the episode is how at each commercial break, Stottlemeyer changes the channel to a basketball game to check the score.
The documentary starts around July 18, when actress Cassandre Rank is found strangled to death in a building lobby. It seems like an interrupted robbery - the police believe that the victim was checking her mail when the killer broke a pane on the door, reached in and opened it, then killed the luckless actress with a rope. After having a few light bulbs fixed on a chandelier, Monk notices an interesting clue: there are glass shards from the door pane on top of the body, but there are none underneath. Also, even though there are traces of Cassandre's lipstick on her coffee cup and on her lips, there is no lipstick in her purse. He concludes that the victim knew the killer, meaning that this was no random attack. He believes that the victim was checking her mail when she saw the killer through the door. She let him in because she wasn't threatened by him and he was someone she knew, which was a big mistake - he killed her, stole her lipstick, and then punched through the door to make it look like a break-in. (In an inserted interview, Stottlemeyer mentions that he didn't tell the press about the missing lipstick; he notes that he does this on major cases because if they do get a confession later on, they'll have an easier time verifying that said confession is genuine.)
The police have no possible leads and no suspects. At this point in time, no one knows that Cassandre's killer will strike again: A few days later, however, another actress, Barbara McFarland, is strangled to death at her apartment. Examining the scene, Monk finds all the same clues, including the missing lipstick and lack of forced entry, that suggest that Cassandre Rank's killer is still at large. Victim #2, like Victim #1, was a part-time actress and waitress.
Monk and Natalie travel to a vampire-themed restaurant that both women had worked at to check out a possible lead. They ask the manager (who keeps slipping in and out of his character as a vampire throughout the interview) for his employment records. However, this lead turns out to be a dead end, as when they receive the employment records, they find that the victims didn't work at the place at the same time.
This isn't the last of it, however: a few days later, victim #3, Miranda Terhume, is strangled to death near her car at a parking lot in Daly City. Once again, all of the clues are the same as those at the first two crime scenes. As she didn't work at the restaurant that Cassandre Rank and Barbara McFarland worked at, that lead has now been declared a false lead.
After several days without a break, Monk makes a keen observation: All three victims of the so-called Lipstick Killer (the name chosen for the man, based on his M.O) had posed for Douglas Thurman, who owns a local photography studio. (In an inserted interview, Monk and Natalie mention that there were 50 cops in that room and they didn't spot the link, and Natalie notes that those cops could have been locked in the room for a year and not noticed the link, though Monk points out to her that he was standing next to the board.) The police bring Thurman in for questioning. As Stottlemeyer and Disher talk to him, he denies everything, although they point out the overwhelming amount of evidence against him.
With insufficient evidence to detain Thurman, they are forced to release him. Things take a startling twist that afternoon - Thurman disappears completely, failing to show up for a polygraph test. A statewide all points bulletin
All points bulletin
An all-points bulletin is a broadcast issued from one US law enforcement agency to another. It typically contains information about a wanted suspect who is to be arrested or a person of interest, for whom law enforcement officers are to look. They are usually dangerous or missing persons. As...
is issued on Thurman, and meanwhile, a judge issues a search warrant
Search warrant
A search warrant is a court order issued by a Magistrate, judge or Supreme Court Official that authorizes law enforcement officers to conduct a search of a person or location for evidence of a crime and to confiscate evidence if it is found....
allowing the police to search Thurman's studio. The next morning, a SWAT
SWAT
A SWAT team is an elite tactical unit in various national law enforcement departments. They are trained to perform high-risk operations that fall outside of the abilities of regular officers...
team raids Thurman's studio and apartment, and they find a rather beautiful incrimination in the studio - an eerie shrine to all three victims, with each woman's portrait having her respective lipstick smeared on it. They determine that they have their man, but Thurman himself has fled (in an interview, Disher admits that this was the low point of the investigation, as they had Thurman in handcuffs just the day before. Stottlemeyer notes that they should have never let Thurman go, but the law is the law - you can't detain someone unless you have enough evidence to suspect probable cause).
Later that same day, Kate Kindel, another model/actress, is found strangled to death at her house, and her lipstick has been taken. All of the clues are the same, suggesting Thurman might not be finished. As Monk looks around, he asks to have a light switch turned on and Novak switches on a lamp next to him. Just then, Stottlemeyer gets a call and learns that Thurman has been spotted in San Racine, in Southern California
Southern California
Southern California is a megaregion, or megapolitan area, in the southern area of the U.S. state of California. Large urban areas include Greater Los Angeles and Greater San Diego. The urban area stretches along the coast from Ventura through the Southland and Inland Empire to San Diego...
, 300 miles south of San Francisco, hiding in a cheap motel
Motel
A motor hotel, or motel for short, is a hotel designed for motorists, and usually has a parking area for motor vehicles...
room. As a SWAT team moves in, Thurman chooses to shoot himself
Suicide
Suicide is the act of intentionally causing one's own death. Suicide is often committed out of despair or attributed to some underlying mental disorder, such as depression, bipolar disorder, schizophrenia, alcoholism, or drug abuse...
rather than be captured. Monk has closed his 100th case, and the episode of “In Focus" wraps up to a round of applause from those at the viewing party.
During the viewing party, however, Monk is becoming a bit doubtful of himself, and is having second thoughts. After the documentary ends, Monk mentions a few oddities about Kate Kindel's death that cast doubt on Thurman being involved there: for one thing, when Thurman killed himself, he had Mexican currency in his pockets, meaning that he was fleeing south, towards Mexico
Mexico
The United Mexican States , commonly known as Mexico , is a federal constitutional republic in North America. It is bordered on the north by the United States; on the south and west by the Pacific Ocean; on the southeast by Guatemala, Belize, and the Caribbean Sea; and on the east by the Gulf of...
, but Kate Kindel was killed 50 miles north of San Francisco. Why would he go that far out of the way to commit a fourth murder, when he knew that the police were after him? Also, Monk remembers that Kindel was strangled from behind while the other victims were strangled from in front.
At Monk's insistence, they rewind the recording of the documentary back to when the SWAT team raids Thurman's studio. Monk notices a crucial detail: when comparing the "before" and "after" shots as the camera moves back and forth across the studio, he spots an additional roll of film in the "after" shot, standing up on the table. The roll is not in the "before" shot, meaning that the roll had been planted. This roll, Disher remembers, was the roll on which the pictures of Kate Kindel were found. Stottlemeyer points out that the SWAT team did not plant the additional roll, as every man on that team is a righteous guy, though Monk notes that there were other people accompanying the SWAT team on the raid.
Then, Monk asks to fast forward to a scene in Kate Kindel’s apartment, in a scene where he asks for someone to turn on the lights. Novak turns on the lamp next to Monk, but suspiciously, in the scene, he knows exactly which switch turns on that specific lamp. Monk concludes that Novak had been in Kindel’s apartment before the investigation.
Earlier in the episode, there have been repeat signs that there is trouble in paradise: Novak flirts shamelessly with several of the women at the party, including Randy's new girlfriend Jillian, an aspiring actress who specializes in being murdered on camera (Randy mentions that she was once bludgeoned to death on Dateline NBC
Dateline NBC
Dateline NBC, or Dateline, is a U.S. weekly television newsmagazine broadcast by NBC. It previously was NBC's flagship news magazine, but now focuses on true crime stories. It airs Friday at 9 p.m. EST and after football season on Sunday at 7 p.m. EST.-History:Dateline is historically notable for...
, and she also appears in the re-enactment scene of Kate Kindel's murder in the show). When he has her in a corner, Jillian acts embarrassed over a gaffe she has made, and Novak soothes her that everyone makes mistakes - his, he confides, was his wife, Melissa.
Here's What Happened
Monk realizes that Kate Kindel was Novak's mistress. She probably threatened to tell his wife about their affair, but whatever happened, he had to kill her. Working on the Douglas Thurman case, Novak saw that he could kill his mistress and make it look like she was one of Thurman's victims. After all, Stottlemeyer notes, Novak and his camera crews had full access to the crime scenes. This meant that they were allowed to know about details that the police withheld from the public, including the killer's M.O.Modus operandi
Modus operandi is a Latin phrase, approximately translated as "mode of operation". The term is used to describe someone's habits or manner of working, their method of operating or functioning...
and the missing lipstick. As a result, it wasn't hard for Novak to frame Thurman for a fourth victim.
Novak knew that the opportunity to frame Thurman for Kindel's murder was the same morning that the police raided Thurman's studio. The night before, he went to Kindel's apartment and had her pose for some photographs. Because Thurman only used film photography, Novak had to use a camera that utilized film. After he took photos of Kindel, Novak killed her, and then staged the scene. He took her lipstick, because that was what Douglas Thurman would have done. The next morning, Novak accompanied the police as they raided Thurman's studio, and he set the roll of film down amongst the other film canisters (the tracking shot itself helped hide him planting the roll, and he was probably aware that as the shot was very quick and brief, no one would notice the extra canister). Kindel would now look like just another rather unfortunate victim of the homicidal photographer.
Novak says there is no proof, but then his estranged wife Melissa produces a lipstick that she found in his pockets on the night of the murder, and demands that the police check it for Kindel's DNA
DNA
Deoxyribonucleic acid is a nucleic acid that contains the genetic instructions used in the development and functioning of all known living organisms . The DNA segments that carry this genetic information are called genes, but other DNA sequences have structural purposes, or are involved in...
. As Melissa hands the lipstick to Randy, Novak pulls out a gun and orders him to hand it over. Randy, exchanging a glance with Stottlemeyer, tosses the lipstick, distracting Novak for the second Stottlemeyer neads to sneak beside him, grab the gun, and deck Novak with a punch. The gun goes off, and Jillian crumples to the floor, clutching her side. Randy panics and yells for an ambulance, but then Jillian realizes that she's untouched, and apologizes, as this is a "force of habit". Randy compliments her on her performance, and the two kiss lovingly - leaving the rest of the company baffled. Novak is subsequently taken away.
The next morning, at Monk's apartment, Natalie reads a front page article about Novak's arrest. Monk, reflecting that one hundred cases is a nice, even number, considers retiring from his detective work. Natalie quickly figures that Monk is not thinking straight, and prepares to whack him with the newspaper. Then she realizes - when Monk caught Douglas Thurman, that was his 100th case. The arrest of James Novak, although related to Thurman and his murders, is a completely different case. Hence, Monk has in fact solved 101 cases. Natalie smugly tells Monk that if he wants to retire, he must solve another 99 cases (200) overall, and they start looking through the paper to see who has been killed over the past day.
Background information
Several of the characters interviewed on "In Focus" reappear after previous episodes, including:- Leigh Harrison (Brooke Adams), a former flight attendant who was forced to quit after being driven to drinking when she had an encounter with Monk (Mr. Monk and the AirplaneMr. Monk and the Airplane"Mr. Monk and the Airplane" is the thirteenth episode of the first season of Monk, and serves as the first season finale.Jason Gray-Stanford listed the episode among his favorites.-Plot summary:...
). - Harold Krenshaw (Tim BagleyTim BagleyTimothy Hugh "Tim" Bagley is an American character actor who has appeared in numerous films and television programs. He is perhaps best known for his recurring roles on the TV series Will & Grace, Monk and $h*! My Dad Says.-Early life:...
), a patient of Dr. Kroger and later Dr. Bell who is obsessed with Monk and is his number one rival (Mr. Monk and the Girl Who Cried Wolf, Mr. Monk and the Election, Mr. Monk Gets a New ShrinkMr. Monk Gets a New Shrink"Mr. Monk Gets a New Shrink" is the seventh episode of the fifth season of Monk, and is the 68th episode overall.Stanley Kamel listed the episode among his favorites.-Synopsis:...
, Mr. Monk and the Daredevil and Mr. Monk Gets Hypnotized. Harold later appears in Mr. Monk Fights City Hall, Mr. Monk Is Someone Else, and Mr. Monk Goes to Group Therapy). - Jimmy Belmont (Ricardo Chavira), a murderer who used salt blocks and a pig to cover up murdering his neighbor Harvey Disher (Mr. Monk Visits a Farm).
- Joey Krenshaw (David KoechnerDavid KoechnerDavid Michael Koechner is an American comedian, musician, and character actor. Koechner began studying improvisational comedy in Chicago at the ImprovOlympic, under the teachings of Del Close, before joining the Second City Northwest...
), a criminal who tried to throw his cousin Harold off a roof (Mr. Monk and the Daredevil). Currently serving ten years for attempted murder. - Hal Tucker (Andy RichterAndy RichterPaul Andrew "Andy" Richter is an American actor, writer, comedian, and late night talk show announcer. He is best known for his role as the sidekick of Conan O'Brien on each of the host's programs: Late Night and The Tonight Show on NBC, and Conan on TBS...
), a murderer who befriended Monk in order to get closer to a crime scene (Mr. Monk Makes a Friend). He murdered his girlfriend Gail Segalis and her previous boyfriend Tim Hayden. - Ralph "Father" Roberts (Howie MandelHowie MandelHoward Michael "Howie" Mandel is a Canadian stand-up comedian, television host, and actor. He is well known as host of the NBC game show Deal or No Deal, as well as the show's daytime and Canadian-English counterparts. Before his career as a game show host, Mandel was best known for his role on...
), a con man who started his own cult in order to get money (Mr. Monk Joins a Cult). - Arlene Boras (Angela KinseyAngela KinseyAngela Kinsey is an American actress. She currently appears as the uptight accountant Angela Martin on the hit NBC television series The Office.-Personal life:...
), who killed her roommate Vickie Deline to protect her fraudulent scheme (Mr. Monk and the Naked Man). Serving life in prison. - Marci Maven (Sarah SilvermanSarah SilvermanSarah Kate Silverman is a Jewish American comedian, writer, actress, singer and musician. Her satirical comedy addresses social taboos and controversial topics such as racism, sexism, and religion....
), Monk's number one fan (Mr. Monk and the TV Star and Mr. Monk and His Biggest Fan). - Ambrose Monk (John TurturroJohn TurturroJohn Michael Turturro is an American actor, writer and director known for his roles in the films Do the Right Thing , Miller's Crossing , Barton Fink , Quiz Show , The Big Lebowski , O Brother, Where Art Thou? and the Transformers film series...
), Monk's agoraphobic brother (Mr. Monk and the Three PiesMr. Monk and the Three PiesMr. Monk and the Three Pies is the eleventh episode of the second season of Monk, and is the 24th episode overall. The episode introduces Adrian Monk's brother, Ambrose. For his performance as Ambrose, John Turturro won an Emmy Award for Outstanding Guest Actor in a Comedy Series. Tony Shalhoub...
and Mr. Monk Goes Home Again).