Real person. Groundbreaking standup comedian. Midge’s mentor and friend.

S1E1 - Flashback: Joel takes Midge to see The Gaiety Traveling Burlesque Road Show, where Lenny performs a bit about kids huffing airplane glue.

S1E1 - Midge is arrested doing her first set, and finds herself in the car with Lenny.

S1E2 - Lenny goes back to ask Midge for cab fare and offers her help with finding a lawyer.

S1E3 - Lenny bails Midge out of jail.

S1E3 - Lenny brings Midge to Susie at the City Spoon Diner, and tells her about his upcoming gig at the Vanguard.

S1E3 - Midge comes to see Lenny at the Vanguard, introducing Lindsey Trent and the Hot Three. After the set, Midge shares a smoke outside with Lenny and the band. Midge smokes her first marijuana joint, and when the band is unexpectedly called back up, Midge steps in for Lenny and does an improvised set. After the gig, as they all head home, Midge tells Lenny that her husband left her, and he hails her a taxi and gives her his extra joint.

S1E7 - When Sophie tells Midge that she needs to have a character on stage, Midge retorts that Bob Hope and Lenny Bruce don’t have characters. Sophie points out that they have dicks.

S1E8 - Susie tricks Lenny into meeting her backstage at The Gaiety Theatre, and talks Lenny into opening Midge at the Gaslight to help her out of her blackballed rut.

S1E8, S2E1 - Lenny opens for Midge at the Gaslight to save her career.

S2E1 - Susie does an interview with Geno Masters and discusses Midge’s relationship with Lenny.

S2E2 - While hiding out from Harry Drake’s goons in the empty Riverside Apartment, Susie smokes the joint that Lenny gave to Midge.

S2E5 - In the Steiner kitchen, Susie mentions to Midge that Lenny is playing Upstairs at the Downstairs the following week.

S2E5 - Midge takes Benjamin to see Lenny. After his set, Midge throws an olive at his head and catches up with him.

S2E10 - Midge runs into Lenny at the Dublin House Tap Room, and the two commiserate about their respective ill fortunes of late. Lenny invites Midge to come see him on Steve Allen.

S2E10 - Midge visits Lenny just before he goes on the Steve Allen show and performs “All Alone.” Watching the performance causes Midge to have a profound realization about her future.

S3E1 - Midge receives a basket of flowers from Lenny, with a note thanking her for coming to his Steve Allen gig. Abe and Rose misinterpret it to mean that Lenny is dating her, and they scold her for leaving Benjamin for a comedian. Midge scorns Abe for not having heard of Lenny, given his delusions of activism.

S3E1 - Spurred by Midge’s earlier criticism of ignorance, Abe goes to see Lenny perform at The Den. Lenny gets arrested by Peluso mid-set, and Abe interferes and gets arrested as well. In jail, Abe waxes poetic about activism and thanks Lenny for the flowers. Rose bails Abe out, and then he persuades her to bail Lenny out as well.

S3E5 - At the Fontainebleau bar, Lenny saves Midge from Andy, who is rather aggressively hitting on her. Lenny mentions that he heard Shy was in town, and wanted to say hi. He then arranges to see her in a couple of days, after some work that he has to do.

S3E5 - Lenny surprises Midge at the bar, and invites her out for dinner and a work thing. She agrees, and the two go to a recording of Miami After Dark, where Lenny is to guest star. In the middle of the show, Lenny unexpectedly pulls Midge on-camera, and the two do an impromptu bit. Afterwards, they eat and dance in a very atmospheric Cuban restaurant. Finally, they finish the evening by returning to Lenny’s hotel. For a moment, it seems as though something more might happen, but Midge pulls back at the last second.

S4E3 - At the Wolford, Midge tries to get a run-of-show list from Boise, but he goes too fast and she fails to keep up. Before she can pursue him for clarification, Lenny surprises her. When she demands that he go away so as not to distract her, he tells her a story about a speech class from his youth and explains that learning to block out distractions is an important part of their shared job. He stays for her show, and along with some companions, pelts her with various objects to test her cool. She does well under the pressure, and the two exchange a playful/approving glance as she leaves the stage.

S4E5 - While taking a cab home from the Wolford, Midge spots Lenny passed out on the sidewalk and takes him home with her.

S4E6 - Lenny wakes up at Midge’s apartment and freaks out. She pursues him, leading to a loud argument outside the building.

S4E7 - Midge watches Gordon interview Lenny about his upcoming Carnegie Hall gig.

S4E8 - Lenny catches Midge’s set at the Wolford about Moishe’s heart attack, and meets her backstage afterwards to apologize for how he left things at her apartment. After some groveling, she accepts his apology, and he excitedly shares the news of his Carnegie Hall gig, and a gig opening for Tony Bennett that he has secured for her. Before Midge can tell him about her “no opening acts” manifesto, the Wolford is raided by the cops and the two are forced to flee out into a snowstorm. After stealing some newspapers to cover their heads, the two shelter in Lenny’s hotel room, and have sex. Afterwards, as they lay in bed, Midge goes into the bathroom and discovers Lenny’s drug pouch. Lenny answers a call from some Wolford people asking to be bailed out of jail, and then discovers Midge looking at his bag. He tells her not to worry about it, that they’ll go spring the riff-raff and then eat some truly terrible Chinese food.

S5E9 - (flashback) Midge and Lenny eat at Wo Hop Chinese Restaurant and discuss what it takes to be famous. Lenny steals Midge’s fortune cookie and pretends that the fortune is forecasting her career success, when it really only has her lucky numbers.

S4E8 - Midge goes to see Lenny perform at Carnegie Hall. He kills. After the show, she meets him backstage, and he pulls her away from the crowd so he can give her a talking-to for declining the Bennett gig. She is obstinate, but eventually he gets through to her and makes her realize that she’s been running down the wrong path.

S5E1 - Midge runs into Lenny at the airport after escorting Alfie there for Susie. The two exchange some strained pleasantries, and he explains that he is moving to Los Angeles. The two exchange a muted farewell in which much is left unsaid, and he turns to go. Struck by a sudden impulse, Midge calls out to him and vows to take the advice he gave her at Carnegie Hall. He walks back up to her and tells her that he’ll hold her to that promise. He looks into her eyes for a moment, then he nods, and the two walk away, never to see each other again.

S5E9 - (flashforward) In 1965, a very strung-out Lenny performs at a club in San Francisco. Susie watches, and goes up to him after the show, offering to use her connections to get him his career back. Lenny declines, and asks whether Midge is there. Susie lies and says no. Lenny shrugs and walks away.

MIDGE: Do you love it?
LENNY: Do I love what?
MIDGE: Comedy. Standup. Do you love it?
LENNY: Seriously? Well, I’ve been doing it a while… okay, let's put it like this. If there was anything else in the entire world that I could possibly do to earn a living, I would. Anything! I'm talking dry cleaners to the Klan, crippled-kid portrait-painter, slaughterhouse attendant… if someone said to me, “Leonard, you can either eat a guy's head, or do two weeks at the Copa,” I'd say “pass the fucking salt.” It's a terrible, terrible job. It should not exist. Like cancer. And god.
– S1E1

LENNY: That looks scary. And familiar.
MIDGE: I have to appear in court.
LENNY: Oh, what's more fun than that? A late-in-life bris, that's more fun.
– S1E3

LENNY: Uh-oh, you need me to be understanding or something? I can pretend to do that.
– S1E3

LENNY: I am doing what is unheard of in this business. It's called a very nice thing.
– S1E8

LENNY: Why did you put a bracelet on with gloves? Do you need to make life harder than it already is?
– S1E8

LENNY: Good evening, ladies, gentlemen, and all the undecided.
– S1E8

MIDGE: You afraid to follow a girl?
LENNY: Always, and everywhere.
– S2E1

LENNY: You're kidding. You went to the Catskills and you bagged yourself a doctor? Your parents must be kvelling.
– S2E5

MIDGE: Two comics walk into a bar…
LENNY: And neither one has any money to pay for the drinks.
MIDGE: Ah, shit, you've heard it before.
– S2E10

LENNY: Well, you know I like you. And, normally, I would do everything in my power to make you feel better. However, tonight, I am feeling very sorry for myself, so all of my sympathy is reserved for me.
– S2E10

LENNY: I'm working to pay all the lawyers. I'm broke. I gave up my apartment, sold my car. Well, I think it was my car. But, either way, it's gone.
– S2E10

LENNY: That's it. Her future spells a murky gloom. I'll be rich and famous, and she'll be living in a furnished room. But it's gonna be too late. I won't hear her moan. I'll be living in my Nob Hill mansion, rich… and all alone. ♪ All alone. All alone. I'll be rich… But so… all… alone. ♪
– S2E10

ABE: Gandhi went to jail. Galileo died under house arrest. Emma Goldman was deported.
LENNY: I just tell jokes, man, that's all.
– S3E1

MIDGE: What on earth are you doing here?
LENNY: I am living here.
MIDGE: In Florida?
LENNY: At some point, every Jew must live in Florida. It's in the Torah.
MIDGE: Wow. You know, it's weird, I never picture you living anywhere. You just exist.
LENNY: Well, sorry to disappoint you, but I do live places, and right now, it's here.
– S3E5

YOUNG FAN: Excuse me, Mr. Bruce?
LENNY: Uh, Mr. Bruce is my mother. “Lenny,” Please.
– S3E5

MIDGE: You're staring.
LENNY: Am I?
MIDGE: Do I have a hair out of place?
LENNY: I didn't know how to tell you.
– S3E5

LENNY: What's the matter? I'm not that bad.
MIDGE: I just can't think of anything funny to say.
LENNY: Yeah. Me, either. It's kind of nice, isn't it?
– S3E5

LENNY: Hey… Maybe someday? Before I'm dead.
MIDGE: It's a date.
– S3E5

LENNY: I got a story for you. Back in high school - Mepham High, in Bellmore, out on Long Island - I took this speech class. One day, the teacher stands me up in front of everybody and gives me a topic - zoos, are they good or bad, some shit like that. I was supposed to be against 'em. Told me to take five full minutes to make my case. Now, I'm feeling fairly confident about the subject, so I start my little spiel, going on about how animals shouldn't be in cages, and how we're the real animals for putting them there in the first place, when all of a sudden, I get beaned in the head by an eraser. I check to see who threw it, and it was the fucking teacher. Now, I'm surprised, to say the least. But I continue my little speech with a masterful segue into the science of evolution and how we're no less animal than any other of God's creatures, that is, if God exists - I threw that in - when another fucking eraser hits me in the fucking head. And it's like that every ten seconds for the rest of my speech, something coming at my head: erasers, chalk, crumpled paper, a half-eaten apple… But I soldier on and get through the five minutes. Afterwards, I ask my teacher, 'What was that all about?' And she says, 'Mr. Schneider,' for I was Schneider at the time, “Mr. Schneider, I was simply training you to block out distractions. It's your job to stay focused, despite whatever's coming at you. And you did good.' This seemed like bullshit at the time, but it turned out to be a very valuable lesson. It trained me for what I do now… So tonight, Mrs. Maisel, your version of erasers and chalk and half-eaten apples will be me staying for your gig.
– S4E3

ZELDA: I need your pants.
LENNY: I need them more.
ZELDA: They are wrinkled. They are bad pants.
LENNY: Well, you just have to get to know them better.
– S4E6

LENNY: Really? In all the times we've been sitting around knitting and making apple dolls while the pies bake in the oven, I've never discussed my child with you? You know why? Because we're not supposed to. That's not how it works. We're comics. Creatures of the night. We discuss debauchery and pornography. We make jokes about dictators coming over for dinner. Ten minutes on how Stalin likes his steak. We don't wear aprons and discuss potty training. If I want to talk about my daughter, I'll call my mother.
– S4E6

SUGAR: Hey, Lenny.
TRIXIE: Hiya, Lenny.
TINA: Nice tie, Leonard.
LENNY: I know them from Hebrew school.
– S4E8

MIDGE: Are you afraid of me 'cause I talk to my shoes? Some men find that wildly attractive.
LENNY: I think there are many things about you men would find wildly attractive.
– S4E8

LENNY: You have a show corset?
MIDGE: Yes.
LENNY: How is this different from, say, your dentist corset?
– S4E8

MIDGE: If we take our clothes off, and we do some very blue things in this very blue room…
LENNY: Wow, do I not know which way this is going.
MIDGE: I need you to look me in the eye first and promise that you will never, ever forget that I am very, very funny.
LENNY: First and foremost.
MIDGE: I'm serious, Lenny.
LENNY: I will be laughing through the entire thing. I promise.
– S4E8

LENNY: Jesus Christ, Midge. What a fucking pedestal you put me on. Getting arrested is not a badge of honor. Getting arrested means I can't work where I want to work. People are afraid of booking me. It's exactly the opposite of what I want for myself. Do you know how much I hate knowing that half the people that come to see me are hoping I'm gonna get popped? Hoping they'll have some great story to tell their friends over cheese and crackers? I want people to fucking laugh. Think and laugh, sure, but laugh. I'm a comic. An entertainer. Baggy pants, banana peels. I'm not the stand-up messiah. This is what I want. This is what I have worked for. Don't you want this? Don't you want to be here? Don't you want to know a thousand mental patients braved a fucking snowstorm to see you? That should be the goal!
– S4E8

LENNY: Do not make this about me. This is about you. You wanted me to remember you're funny, right? That night? You didn't want me to think of you as just a girl. You wanted me to think of you as a comic. Well, don't you forget that I'm a comic, too. Don't you dare look at me as someone to be pitied or helped or fixed. I do not want or need that, especially from you.
– S4E8

LENNY: Don't plan! Work. Just work, and keep working. There is a moment in this business… windows open. If you miss it, it closes. Just don't… If you blow this, Midge, I swear… you will break my fucking heart.
– S4E8

MIDGE: Well… I… think you'll really enjoy L.A. With all the… sun and… oranges and Disneyland. All the things you love.
LENNY: Oh, I'm sure I'll find a cloud or two to hide under.
– S5E1

LENNY: You mark my words. Very soon, in the not too distant future… you will be paying for the Chinese food.
– S5E9

1. Pilot
2. Ya Shivu v Bolshom Dome Na Kholme
3. Because You Left
8. Thank You and Good Night

1. Simone
5. Midnight at the Concord
10. All Alone

1. Strike Up the Band
5. It's Comedy or Cabbage

3. Everything is Bellmore
5. How to Chew Quietly and Influence People
6. Maisel vs. Lennon: The Cut Contest
7. Ethan...Esther...Chaim
8. How Do You Get to Carnegie Hall?

1. Go Forward
9. Four Minutes

• Luke Kirby also appears in the Palladinos’ subsequent series, Étoile.

• Kitty Bruce, the real-life daughter of Lenny Bruce, has stated on multiple occasions that she is very happy with her father’s portrayal in the series. During the filming of the second season, Kitty was invited to visit the set and meet Luke Kirby and Rachel Brosnahan, which she did.

• List of Characters