THE POUR DECISION: A MURDER MYSTERY EXPERIENCE 

CHARACTERS 

Thomas “Tommy” Callahan – The Patriarch 

Vivian “Viv” Callahan – The Bitter Ex 

• PERSONALITY: Lucille Bluth energy — sharp-tongued, boozy, elegant, and cutting. Always has a glass in hand and a withering remark ready. 
• MOTIVE: Tommy was going to cut off her alimony and leave everything to charity (or someone else). She may have “helped” with his last drink. 
• KEY HOOKS: Roasts everyone, complains about the wine pairings in character, perfect for big dramatic scenes and audience banter. 

Finn Harrington – The Step-Son 

• PERSONALITY: Fancy, entitled, “old money” try-hard. Armani suits, but secretly drowning in gambling/sports-betting debts to the wrong people. 
• MOTIVE: Needs the inheritance to pay off bookies before his legs get broken. Already “borrowed” from the bar accounts. 
• KEY HOOKS: Preppy one-liners, desperate charm, great for physical comedy and “I’m fine, everything’s fine” energy. 

Skye “The Vibe” Summers – The Influencer 

• PERSONALITY: Wannabe TikTok/Instagram star who constantly rebrands (Gothic Griefcore today, Tradwife Detective tomorrow). Films everything, terrible edits, cringy dances. 
• MOTIVE: Shay threatened to cut off her funding and expose her fake followers / shady sponsored posts using the family name. 
• KEY HOOKS: Constantly filming the wake for “content,” bad ring-light moments, audience can join (or boo) her TikTok challenges. 

Cormac “Mac” Callahan – The Half-Brother 

• PERSONALITY: Charismatic but perpetually half-drunk schemer with classic “Job” Bluth energy. Flashy, overly confident in his terrible ideas, and quick with big gestures and dramatic declarations. Has spent years feeling like the “backup son.” He masks his hurt with sarcasm, failed power plays, and increasingly sloppy attempts to look in control. 
• MOTIVE: He wants the bar. Badly. Mac believes he’s the one who actually kept the place running while Tommy coasted on charm and favoritism. He’s convinced the inheritance (and control of the business) should go to him — the son who “actually showed up.” The resentment that “Mom always loved Tommy best” fuels almost everything he does. 
• KEY HOOKS: Bitter one-liners about family favoritism that get darker the drunker he gets. Physical comedy gold — big theatrical gestures that devolve into stumbling. Tries (and fails) to play the smooth businessman while clearly unraveling. Perfect for slurred monologues and desperate last-minute schemes.

Cherysh “Cherry” Callahan – The Trophy Ex 

• PERSONALITY: The ultimate trophy ex-wife — semi-gorgeous, vain, and cheerfully dim. She has that classic Loretta-from-Cheers airheaded charm mixed with a touch of self-absorbed cluelessness. She speaks in simple (sometimes hilariously wrong) statements, loves being the center of attention. 
• MOTIVE: Money and status. She wants a big piece of the estate (or at least a fat alimony settlement) because she “put up with Tommy for years” and believes she’s owed it. She doesn’t have a complex plan — she just wants what she feels she deserves as the “pretty one.” 
• KEY HOOKS: Perfect verbal sparring partner for Viv (“You’re old.” “You’re dumb.”). Their scenes should be vicious and hilarious. Constant malapropisms and misunderstandings that accidentally land on truth. Physical comedy through her “trophy wife” presentation — hair flips, poses, and oblivious flirting. Can have surprisingly cutting moments when her ego is threatened. 

The Waitress – The Observer 

• PERSONALITY: Deadpan, hyper-observant, and quietly intelligent. She’s trying to stay professional and get through her shift, but she can’t help noticing every lie, inconsistency, and character flaw in the room. She has a dry, slightly sarcastic sense of humor that slips out when she’s refilling drinks or clearing plates. She’s not trying to be the hero — she’s just naturally good at reading people and patterns. 
• MOTIVE: She has no stake in the murder or the inheritance. Her only real goal is to survive the shift, make her tips, and gather material for the mystery novel she’s secretly writing. The chaos around her is basically free research. 
• KEY HOOKS: Drops subtle but sharp observations while serving (“Interesting how everyone’s alibi falls apart right when the apps hit the table…”). Mixology and forensic psychology minor give her great one-liners about drinks, evidence, and human behavior. Becomes the audience’s eyes and ears — the one character who actually sees what’s happening. Can break the fourth wall slightly with meta comments about “how this would play in a book.” Her growing frustration with the family’s nonsense is comedy gold. 

AUDITION MONOLOGUES 

These monologues are in the style of a “toast” to the deceased patriarch Tommy Callahan, who owned the bistro and died a very wealthy man. 

Vivian “Viv” Callahan – The Bitter Ex 

VIV: Oh, Tommy. Tommy, Tommy, Tommy… (shakes her head, composing herself and raising a glass of wine) To Thomas Callahan. My late husband. The patriarch. The man who could turn an average corner wine bar into the kind of miracle where people happily pay twenty dollars a glass for the privilege of drinking his personality. He did have success, didn’t he? Tommy’s rampant charm was like fly paper to investors, patrons, ex-wives — he attracted them all (aside: and disappointed them almost as quickly.) Tommy had that rare and precious gift revered by

politicians and ponze-schemists all over the world: he could make you feel that — of all the people in the room — you were the most important person he’d ever met. 

I don’t wish to speak ill of the dead, but one cannot recognize Tommy’s brilliant successes without also acknowledging his brilliant failures. Tommy’s failures piled up like unpaid bar tabs. Multiple failed businesses, failed marriages — I was simply the first in a long line of women who learned that Tommy’s promises came with a very short expiration date. Children who somehow inherited the looks, the attitude, and none of the follow-through. Grand plans for marriage and family that resulted in a stack of unpaid bar bills with no one left to pay the tab. Tommy is now gone, leaving us with the memory of his charm, brilliance, and unpaid tabs… may he rest in peace. Though, knowing Tommy as I did, I find that unlikely. 

(Raises glass) 

To Tommy. May the afterlife have better wine selections than whatever we’re drinking tonight. (To TOMMY) Though, between us… I always suspected your last drink would be the one that did you in. 

Finn Harrington – The Step-Son 

FINN: To Tommy. Or… Mr. Callahan. Though we were not related by blood, I always thought of you as my father. My Dad. My real Daddy — not Daddy — but, you were like my Dad. Not my step-dad, my actual father figure. So, so much more than a, uhm — step-father figure. 

(changing tactics) 

Boy, he was a real success story, wasn’t he? Built this place from nothing. Turned Pour into… well, into Pour. The man had charm. Real charm. The kind that makes investors open their wallets and customers feel like they’re part of something special. He always said the secret was making people feel important. And he was right. Look at this turnout. Even dead, he’s still the most interesting person in the room. 

(small, nervous laugh that dies a little too fast) 

Of course, there were… challenges. The businesses. The marriages. I always liked to think that of all Tommy’s step-children, I was his favorite. He always had a plan. Always said he’d take care of the people who mattered. The ones who showed up. The ones who were loyal. 

I just… I know he wouldn’t have wanted anyone to worry about the practical things. The future. Money. All that stuff. He was a visionary. He thought big. And he always said family takes care of family. 

(He takes a sip of wine — a little too quickly — then forces the smile back on.) 

To Tommy. May he rest in peace. And may the rest of us… figure out how to honor what he built. Together. Like he would have wanted.

Cormac “Mac” Callahan – The Half-Brother 

MAC: To Tommy. My brother. My half-brother. The golden boy. The one who could walk into a room and make everyone feel like they’d been waiting for him their whole life. 

(He takes a drink, then keeps going, voice getting a little louder.) 

You know, growing up, Mom always said Tommy was the one with the real potential. The charm. The vision. Me? I was the one who actually showed up. I was the one who knew how the bar actually worked — the vendors, the staff, the numbers. But every time I brought him an idea — whiskey tasting nights, two-for-one drinks for Realtors on Thursdays, strip-poker after hours — he’d smile that big Tommy smile and say, “We’ll circle back, Mac.” Like I was some kid with a lemonade stand. 

(He laughs once, but there’s no humor in it. He takes another drink.) 

And now he’s dead! God rest his soul. What will we do without Tommy Callahan’s generous charity and magnanimous charm? Oh, how will we ever survive, am I right? (Laughs a few times, as his tone becomes suddenly darker) But, ah, seriously, though… Mom always loved Tommy best. Why I’ll bet if she was here right now, she’d be saying, (Irish accent) “Poor Tommy, he was the best son a mother could ever have… never another like my Tommy. Never!” Never mind that I was the one actually keeping the damn dreams running, Mom! I had great ideas too, you know, but you never could see— 

(He catches himself, forces a tight smile, and lowers it again.) 

But hey… that’s family, am I right? You do all the work, and the charming one gets all the credit. And all the money. And all the wives, and… everything. 

(He raises his glass toward the body) 

To Tommy. May he rest in peace. And may the rest of us finally get a chance to do things the way they should’ve been done all along. 

Skye “The Vibe” Summers – The Influencer 

SKYE: Okay everyone, we are live from the wake. I just… I can’t even right now. Like, the energy in this room is so heavy, but also… so beautiful? It’s giving main character energy meets ancestral healing. Tommy was… he was more than just my… whatever he was to me. He was my mentor. My vibe guide. My… financial… supporter. And now he’s gone and I’m just… processing. 

(She turns the camera slightly toward Tommy’s body, then back to herself.) 

I’ve been sitting with this all morning and I just keep thinking… what would Tommy want? And the answer is so clear. He would want me to share this. He would want me to turn this pain into

content. Because that’s what he taught me. He always said, “Skye, the world needs your light.” And I’m like… “But Tommy, what if my light is too bright?” And he was like… well, he didn’t really say anything back, but I felt it. 

(She wipes under her eye even though there are no tears, then looks directly into the camera.) 

If you’re watching this and you’re grieving too, drop a �� in the comments. And if you’re not grieving but you’re vibing with my journey, hit that follow button because we’re about to go on a healing journey… together. 

(She takes a moment, eyes closed, deep breath…) 

Anyway. To Tommy. You were… you were everything. Except when you weren’t. And that’s okay. Growth is… messy. Healing is messy. And sometimes… sometimes the people who fund your entire lifestyle threaten to cut you off and expose your follower count and you just have to… pivot. 

(She raises a glass toward the body with one hand while still holding her phone in the other.) 

To Tommy. My sort-of-like Father. May you rest in your truth. May you rest in your authentic peace. And may we all remember to live authentically, post responsibly, and never let anyone dim our light. Do we have time for a song? No, we’ll do that later. I’m not sure I can handle singing right now. Emotionally. 

(She turns back to the camera, somberly.) 

Don’t forget to like, comment, and subscribe. And if anyone has Tommy’s old Rolex, I’m manifesting it for a “grief unboxing” video. Bye for now. And remember: the journey is the journey. Peace. 

(She stops recording, immediately checks the footage, and mutters to herself.) Ugh, the lighting in here is criminal. 

Cherysh “Cherry” Callahan – The Trophy Ex 

CHERYSH: Hi everyone. For those who don’t know me, I am Cherysh. With a “y”. I was one of Tommy’s wives. In fact, Tommy always used to say I was his “favorite Ex.” 

(She flips her hair and gives a little practiced smile to the room, clearly expecting everyone to be impressed.) 

I mean, he had a few of us, but I was the one who really got him. It wasn’t always easy. Tommy was a lot to deal with… his late nights at the bar, his “business trips,” his other wives… but I never complained. Well, not too much. Because I’m a lady. And ladies don’t make scenes. Even when their husband is… you know… generous with his attention.

(She glances at Tommy’s body and sighs dramatically, hand to chest.) 

Tommy always said I was his favorite Ex. He said I was both the prettiest AND the sweetest. I was the one who looked best on his arm. And I think that’s important. Looks matter. Especially when you’re married and you’re building something together. Or… when you’re divorced and you’re not building something together but you still deserve to be taken care of because you were taken care of even though you were the last in a long line of tramps and harlotts that only loved you for your money but I loved you for you! And I think that’s worth something, isn’t it? 

(She adjusts her dress and poses slightly, like she’s on a red carpet instead of at a wake.) 

I always told him, “Tommy, if anything ever happens to you, I hope you remember who stood by you when things were hard.” And he would just smile and say, “And nobody makes me harder than you.” Which I took as an un-equivical yes. 

(She raises her glass toward the body with a bright, empty smile.) 

So… to Tommy. You were… a lot. But I was your favorite. And favorites should be remembered. In the will. And in the pictures. And with… you know… money. Because that’s what love is, really. Being remembered properly. 

(She takes a dainty sip, then lowers the glass and adds, almost as an afterthought:) 

Also, if anyone finds his Rolex, I’m pretty sure he wanted me to have it. He said so. Once. Kind of. 

The Waitress – The Observer 

(Table-side speech) 

WAITRESS: Hi, welcome to Chilis. I mean— welcome to Pour! Sorry, I’m really nervous. I’ll be taking care of you tonight. It’s my first night on the job and my first night at an Irish Wake, so… don’t be surprised if I screw everything up! 

(She laughs and smiles, then suddenly:) 

I’m not a full-time waitress, by the way — I’m actually studying to be a detective. My mom always says I’m WAY too nosy, so I figure this will be a good way to put my “nosy” skills to good use. I mean, my hunches and observatory skills are like — top notch. When I was a kid, I once figured out who stole a cupcake from the kitchen counter by surreptitiously smelling everyone’s breath. (Looks both ways, then whispering) It was my dad! Anyways, I don’t know how you know Tommy, but have you noticed anything strange about this wake so far? Like, my Spidey senses

are just a-tingling! Did you notice how quickly everyone started talking about the will? One minute they’re toasting him, the next they’re dividing up the bar like it’s a game of Monopoly and someone just landed on Free Parking! My family always plays with money on Free Parking, doesn’t yours? Makes the game WAY more interesting— 

(She catches herself again.) 

Not that it’s any of my business — I’m just here to pour drinks and clear plates. That’s it! No investigating. No theorizing. No quietly building a suspect list in my head while I refill water glasses… 

(She pauses one more time, then adds, almost to herself:) 

Even though that one guy keeps checking his phone like he’s expecting a very expensive phone call. And that girl with the ring light has been filming herself and the body from like three different angles — what’s with that during a wake? Oh, and the beach ball bimbo who insists she was his “favorite Ex” keeps glancing at the body in fear… as if the corpse itself may come alive and 

accuse her of MURDER! I mean, has anyone mentioned that Tommy …may have been murdered? Maybe it’s just me. . . 

(She straightens up, tray in hand, and offers a bright, slightly strained smile.) Anyways. Can I get anyone another drink?