When Apple TV+ first debuted on November 1, few series were as welcome a surprise, or as critically acclaimed, as Dickinson, starring Hailee Steinfeld. A super modern sitcom, with darkly comedic and often inappropriate flair, the series is a loose but still accurate adaptation of the life of a young Emily Dickinson, the famous 19th-century poet from Amherst, Massachusetts.

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The series is framed as a coming of age story and finds Emily experiencing love and loss over the course of her artistic journey as she struggles to make her name known as a poet. But along the way, Emily makes plenty of friends - and even a few enemies, too - who have some strikingly familiar faces. We're taking a look back at the best guest stars who popped up in the series' first season.

Robert Picardo (Ithamar Conkey)

Robert Picardo in Dickinson

Certain characters exist in a series to provide background and depth to main characters' storylines, even if they seldom receive much attention on their own. Robert Picardo's role of Ithamar Conkey, a friend and advisor to the Dickinson family patriarch, is one such role, but Picardo's brilliant comedic timing elevates the role to something much more - especially when he is given a bawdy, over the top romance storyline in later episodes.

One of the most prominent working actors in the current age of television, Robert Picardo is perhaps best known for his work in multiple series within the Star Trek universe, including the Doctor in Star Trek: Voyager. He also appeared in the iconic 1990s series The Wonder Years, and had another prominent science fiction career in the Stargate universe.

Jessica Hecht (Aunt Lavinia)

Jessica Hecht in Dickinson

Just like most of your favorite sitcoms, Dickinson includes a Christmas celebration episode toward the end of its first season. It's this episode that introduces viewers to a more expansive cast of characters attending the Dickinson family festivities, including Jessica Hecht's Aunt Lavinia, the namesake of the younger, ditzier Dickinson daughter. Lavinia is frank and flirtatious, and over the top - so it's not hard to see how the name carried on much more than just a name across the generations.

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Jessica Hecht is best known for her career as a talented character actress, but also as a Broadway star. On the small screen and silver screen, she's best recognized as Susan Bunch, Ross's ex-wife's new wife on Friends; Walter's former chemistry partner Gretchen Schwartz on Breaking Bad; and for her recent cameo as Matthew Rhys' character's mother in A Beautiful Day in the Neighborhood.

Zosia Mamet (Louisa May Alcott)

Zosia Mamet as Louisa May Alcott in Dickinson

It's also the Christmas episode that introduces another literary icon into Emily's orbit: none other than Louisa May Alcott, the genius mind behind Little House on the Prairie. As played by Zosia Mamet, Alcott is one of the most modern and forward-thinking characters in the series. Already an established author, Mamet's Alcott has no time for the patriarchal society in which they live and gives Emily some much-needed words of inspiration for pursuing her own writing career.

Prior to her hilarious turn as Louisa May Alcott, Zosia Mamet made a name for herself as the scene-stealing ditz Shoshanna Shapiro in Lena Dunham's polarizing HBO sitcom Girls. The daughter of acclaimed playwright David Mamet, Zosia Mamet has also had supporting roles in various mainstream series, both drama and comedy, including Unbreakable Kimmy SchmidtMad MenTales of the City, and Parenthood.

Matt Lauria (Ben Newton)

Matt Lauria in Dickinson

As Emily nurses her broken heart over the seeming loss of her intimacy with longtime best friend Sue, Ben Newton enters her life. Played with charming aplomb by Matt Lauria, Ben is a law student working under her father's guidance. He also happens to be an expert on literature, an ardent supporter of Emily's poetic ambition, and a fellow "freak" and outsider, which leads to the two of them hitting things off both platonically and romantically, before Ben sadly dies of tuberculosis near the season's end.

Before he was winning and breaking hearts as the lovable Ben Newton, Matt Lauria was perhaps best known for his work in the acclaimed MMA focused series Kingdom on the Audience Network. Prior to that, Lauria appeared in the final two seasons of critic and cult fan favorite Friday Night Lights as Luke Cafferty, and as Mae Whitman's character Amber's troubled love interest Ryan York in Parenthood.

John Mulaney (Henry David Thoreau)

John Mulaney as Henry David Thoreau in Dickinson

A few years after remarking in one of his stand up specials that he was certain Emily Dickinson was a lesbian, John Mulaney got to put his beliefs to the test when he appeared in the series as none other than the renowned author and theorist Henry David Thoreau. In the fourth episode of the season, "Alone I Cannot Be," Emily sets out to meet Thoreau, a writer whose work she inspires, only to find Mulaney's Thoreau to be a total jerk who even harshly warns her to never meet her heroes.

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In addition to his extensive work in stand up comedy, including multiple specials that have been released on Netflix, John Mulaney is best known for his work on series like Big MouthComedy Bang! Bang!MulaneyThe Jim Gaffigan ShowPortlandia, and many more. He served as a staff writer for Saturday Night Live for a decade, and recently appeared as Spider-Ham in Spider-Man: Into the Spider-Verse.

Jason Mantzoukas (The Bee)

Jason Mantzoukas Bee in Dickinson

Dickinson as a show is absurdist and fantastical in many ways. But very few of those ways are as hard to believe as the inclusion of a hallucinated, human-sized, anthropomorphic bee voiced by Jason Mantzoukas. The bee, as he's simply known, appears three times throughout the season, whether Emily is high or simply having a truly absurd dream, and each and every time, he's completely over the top and completely on brand for Mantzoukas, too.

One of the wildest and weirdest comedians working in Hollywood right now, Jason Mantzoukas is definitely an actor you can classify as "that guy you know from that thing." A veteran character actor, Mantzoukas has appeared on stand up and improvisational comedy focused series like Comedy Bang! Bang!Drunk History, and Kroll Show. He's portrayed iconic characters on various television shows, including Adrian Pimento on Brooklyn Nine-Nine; Jay Bilzerian in Big Mouth; and Derek Hoffstetler in The Good Place.

Wiz Khalifa (Death)

Emily resting her head on Death's shoulder

Perhaps the biggest and best surprise to come out of Dickinson in terms of its truly stellar casting department was the choice to use famous rapper Wiz Khalifa in the role of Death. Emily proudly proclaims early in the series' first episode that she is in love with Death, and that he comes for her every night. Across the series, viewers are treated to various encounters between Emily and her morbid quasi-suitor, and each scene only works so well because of Khalifa's inherent grasp of the darkly comedic material.

Of course, Khalifa is undoubtedly best known for his rapping career. Between 2006 and 2018, he released seven albums, and has collaborated with artists including Snoop Dogg, Travis Scott, Ty Dolla Sign, and Lil Uzi Vert. His short filmography also includes appearances on Punk'dRidiculousness, and The Eric Andre Show.

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