Monkhad a lot of guest stars throughout its eight-season run, two of whom won Emmys for it and played surprisingly similar characters. As an episodic procedural where Adrian would solve a different murder every week,Monkhad the chance to introduce a lot of different characters for one-off appearances. As a result, the show featured several guest stars, many of whom were fans of the series or had some connection to the cast ofMonk. For example,Stanley Tucci starred alongside Tony Shalhoubin 1996’sBig Night.
Some ofMonk’s greatest characters were played by guest stars, from villains to friends or family of Adrian Monk. For example, comedianAndy Richter played one ofMonk’s best villains. That is not to mention the appearances from actors who had yet to have their breakout roles in the industry, the most famous example being Jennifer Lawrence. However, of all the special appearances and cameos inMonk, two stand out and were more than deserving of winning Emmys for Outstanding Guest Actor In A Comedy Series – John Turturro and Stanley Tucci.

John Turturro And Stanley Tucci Were Both Playing Versions Of Adrian Monk
Ambrose Was Monk’s Brother; David Was An Actor Playing Monk
John Turturro’s Ambrose Monkand Stanley Tucci’s David Ruskin were both alternate versions of Adrian Monk for different reasons. Ambrose Monk appeared for the first time in “Mr. Monk and the Three Pies,” during which we are introduced to Adrian’s brother and learn more about what Monk’s life as a child looked like.Ambrose Monk has OCD as well as agoraphobia, having not left his house in decades. While Adrian and Ambrose would say he and his brother were nothing alike, they were very similar in more than just one way.
Tony Shalhoub won two Outstanding Lead Actor In A Comedy Series Emmys for his role as Adrian Monk.

Stanley Tucci played a more meta character inMonk. David Ruskin was an actor hired to play Adrian Monk in a film based on the astronaut case, which Monk was very excited about until he realized Ruskin was a dedicated method actor. To play Monk, David Ruskin had to become Monk. More than dressing like Adrian or copying his gestures, Tucci’s character wanted to understand how Monk’s mind worked. By the end of the episode,David Ruskin actually believed he was Adrian Monk.
Turturro And Tucci Stole The Show With Their Guest Appearances In Monk
Turturro And Tucci Gave Emmy-Winning Performances In Monk
It’s no coincidence that the two best guest stars inMonkwere both sort of playing alternate versions of the show’s titular character. Ambrose Monk and David Ruskin worked as mirrors, allowing Adrian to see himself in others. Likewise, we, the audience, got to see Monk through different lenses with the help of those characters.Turturro’s performance as Ambrose was incredibly sweet yet also tragic, which are terms that also describe Adrian Monk.
Jennifer Lawrence’s Blink-And-You-Miss-It Role In Monk Is Even Better Once You Learn The Story Behind It
Jennifer Lawrence famously appeared in an episode of Monk before she broke big, and the story behind her role on the show makes it even better.
Tucci’s character explored the more vicious side of Adrian Monk– someone who would not rest until he found the closure he was looking for. Interestingly, Adrian struggled to see himself in Ambrose and David Ruskin’s version of Monk. In “Mr. Monk and the Actor,” Natalie even called out how knocking on someone’s door in the middle of the night, which Ruskin had done, was the same thing Monk was doing to her. Characters like Ambrose and David elevatedMonkand stole the show in their respective episodes, even outshining the case of the week.
Monk
Cast
Starring Tony Shalhoub as Adrian Monk, Monk follows the titular detective, a private investigator with OCD who helps solve crimes with the San Francisco Police. On the side, he also investigates the death of his wife, who was killed by a car bomb. Bitty Schram, Traylor Howard, Ted Levine, and Jason Gray-Stanford also star.