If Dickinson’s first season was a treat, the currently airing second season is a feast. Apple TV+’s anachronistic comedy about the teenage years of Emily Dickinson (Hailee Steinfeld) is a tonal wonderland, shifting from surrealist fantasy one moment to achingly grounded the next. But throughout the series, one thing has stayed consistent: the delightful ensemble of guest stars. As unpredictable as the show itself, the casting decisions often feel equally comical and cunning in this experimental look at a literary icon and the world around her.
From half the cast of Big Mouth to a rapper behind three contributions to Fast and Furious soundtracks, the Dickinson guest cast is as lit as that “Wild nights” rager from season one. Read on to see how the scene-stealers stack up, in this ranking of Dickinson’s 14 best guest stars so far.
14. Robert Picardo as Ithamar Conkey
While Robert Picardo may be best known for playing The Doctor, who supported the Star Trek: Voyager crew in medical matters, now he plays Ithamar Conkey, who supports Dickinson’s patriarch Edward (Toby Huss) in matters of… business? Politics? General life advice? I honestly am not quite sure exactly what the span of Conkey’s duties are, but I do know that he’s a bawdy old man who has a very big top hat, very teensy glasses, and a very big appetite for ham. What more information could one possibly need?
13. James Urbaniak as Emily’s Opthamologist
I’ve never found a show that couldn’t benefit from the addition of James Urbaniak, and it’s quite unlikely that such a show even exists. Though The Venture Bros. and Difficult People star doesn’t get much screen time in Dickinson’s second season, Urbaniak still manages to get in several memorable line deliveries during his brief cameo as Emily’s opthamologist in the season two premiere. And given the warning that Emily’s eye troubles will only worsen over time, we’re hoping this means Urbaniak might return to the Apple TV+ series down the line.
12. Kelli Barrett as Adelaide May
The Fosse/Verdon alum trades in her bowler hat for opera gloves in season two’s “Split the lark.” When the Dickinson family attends the opera, Emily takes the opportunity to sneak backstage to meet the star Adelaide May. Played by Kelli Barrett, Adelaide is far from the passionate artist who transfixed Emily on stage. Instead, Adelaide is a jaded woman, hardened by a life in showbiz, who doles out some harsh warnings about the underbelly of fame. Just like May leaves a strong impression on Emily, Barrett leaves one on viewers, and the actress helps make “Split the lark” one of Dickinson’s most memorable episodes to date.
11. Will Pullen as Nobody
Though Dickinson is largely an extremely silly show, the second season has a mournfully serious throughline as Emily is forced to confront questions of the cost of fame and immortality. These fears are embodied in the mysterious figure of Nobody (played by The Americans’ Will Pullen), an eerie specter who haunts Emily throughout the season. Dickinson often will use one of poet’s works as inspiration for a single episode. That's why it’s been exciting to see one of Dickinson’s most famous works, “I’m Nobody! Who are you?” be explored so thoroughly, with Pullen affectingly personifying the poet’s complicated relationship with fame.
10. Finn Jones as Samuel Bowles
Finn Jones is perfectly smarmy as Sam Bowles, a successful newspaper publisher who exemplifies all the trappings of a faux feminist ally. Though Sam is known for publishing female writers, a rarity in those times, and is set on helping Emily achieve fame, he relishes lording his power over her, negging Emily and manipulating her into believing he alone holds the key to her dreams. Bowles’ confidence in Emily is intoxicating to the young poet, and Jones brings enough magnetism to the role that I can (somewhat) understand why Emily is so desperate for his approval — even though it’s disturbingly clear that this man is neither the Daisy nor the Sun.
9. Jessica Hecht as Aunt Lavinia
Many viewers first became familiar with Hecht as Friends’ Susan Bunt, but now she appears off-and-on in Dickinson as Lavinia, Emily’s aunt who is riding the high of her “widow’s euphoria” all around Europe. As horny as Samantha Jones and as crunchy as Shailene Woodley, Aunt Lavinia comes with a guarantee that whenever she pops up in an episode you’re in for a raucous time. Here’s hoping season three features Lavinia taking her nieces on one of her legendary cruises. (I think her namesake would quite enjoy it.)
8. Nick Kroll as Edgar Allan Poe
Whenever Dickinson decides to put its spin on another famous author from Emily’s time, I assume the series has something delightful in store for. This theory once again proves correct when Nick Kroll appears in season two’s “I’m Nobody! Who are you?” as “the great and recently late” Edgar Allan Poe. When Emily joins Poe and Death (Wiz Khalifa) for a carriage ride, Kroll hams it up as the presumptuous author, whose shamelessly shallow afterlife and dismissal of Emily’s small success gives her another perspective on fame — and gives viewers yet another entertaining scene dismantling the myth of a literary giant.
7. Timothy Simons as Frederick Law Olmstead
While Timothy Simons will always be Jonah “Jonad” Ryan from Veep in the deepest core of my soul, he carves out a new space for himself in my heart thanks to his appearance in Dickinson’s “The Daisy follows soft the Sun.” In the episode, the actor plays Frederick Law Olmstead, the famed landscape architect who comes to Amherst to design the town common upon a request from Austin Dickinson (Adrian Blake Enscoe). As portrayed by Simons, Olmstead is matter of fact, unorthodox, and weirdly sexy. (That mustache is working for him, what can I say?) He’s also crucial to helping Emily overcome her writers’ block, all while getting off incredible lines like, “This rock is making exactly the right statement,” and convincing me that a rosebush is the missing key to healing the abuses of my deafening urban life.
6. Ayo Edebiri as Hattie
A true multi-hyphenate, Hattie is a maid, medium, writer, singer, florist, and one of the best additions to the show’s sophomore outing. Playing this freelancer icon is Ayo Edebiri, a comedian who speaks to the heart of all of our — Okay, maybe just my — driving desire when Hattie declares, “I want to make spooky shit happen and get paid.” Though Hattie is more often on the peripheral of the storylines, she devours the dialogue (which Edebiri, a writer on the show, also helped craft) and has me hoping Hattie will take on a more central role moving forward.
5. Matt Lauria as Ben Newton
When Emily meets Ben in the back half of the first season, it’s immediately understandable why she falls so quickly for her father’s law clerk. Matt Lauria brings such warmth to the part that it becomes easy to imagine a future where the non-husband and non-wife might find a way to build a happy life together — even if they each still pine for others. It doesn’t hurt that Emily and Ben’s brief romance features so many rom-com worthy moments, like their adorable meet-cute during her feigned illness and Ben giving Emily an annotated book like he’s a 19th century Jess Mariano. That's why when Ben dies from tuberculosis only a few episodes after his introduction, fans became nearly as heartbroken as Emily to say goodbye to his charming presence.
4. Jason Mantzoukas as The Bee
The absurdist brilliance of Dickinson is perhaps best crystallized in this mind-bogglingly great guest casting, in which Jason Mantzoukas lends his voice to a big bee that a very high Emily hallucinates. The two slow dancing together in “Wild nights” is perhaps the best unintentional advertisement for doing opium I’ve ever seen, if only so that I could be on the receiving end of Mantzoukas explaining why he’s so sweet (“I’m covered in pollen, baby”). Fortunately, Dickinson realized the power of The Bee and has found ways to bring him back, no opium necessary. And each time this gigantic insect has popped on screen, we’ve been all the better for it.
3. Zosia Mamet as Louisa May Alcott
Bless this show for finding a way to have Louisa May Alcott show up at a Dickinson family Christmas party, and bless Zosia Mamet for delivering one of the show’s funniest performances yet. Though she only appears in a single episode, I will never soon forget Mamet’s Alcott delivering lines like "I love to run. That's an actual fact about me,” or "Okay, yeah, but stick with me, what if one of the sisters dies?" While we doubt the Little Women author was as riotously kooky as the Dickinson version, it’s delightful to see the show portray a female writer who's so completely different from Emily — one who has no interest in romance or her family’s approval, just cold, hard cash.
2. Wiz Khalifa as Death
Before Dickinson had even premiered, we were given a hint at the surprising casting decisions to come when it was announced that Wiz Khalifa would be taking on the role of Death. The unexpected choice proved to be an ingenious one, with the rapper embodying the seductive and aloof reaper of souls who has ownership over Emily’s heart. Whether delivering a harsh dose of reality to Emily or tossing off a biting one-liner, Khalifa plays Death to perfection. His performance is hypnotic, wry, and stylish, and he's the reason I'll never tire of the recurring sparring matches between Death and his biggest fan.
1. John Mulaney as Henry David Thoreau
While I enjoyed the first few episodes of Dickinson, I have to admit that initially the main reason I continued watching was so that I would make it to the episode where John Mulaney plays Henry David Thoreau. This is a casting with pull to it. In season one’s “Alone, I cannot be,” Emily discovers the dangers of meeting your heroes when she travels to Walden to meet Thoreau. But rather than the author being the introspective recluse Emily expects, she’s met by a pompous blowhard with a bedraggled beard whose attempts at performative isolation are literally laughable. Mulaney thrives in the role, making a comedic meal from each moment he’s on screen and delivering a perfect reconsideration of Thoreau that’s far closer to who the author truly was, rather than how he portrayed himself to be.
