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The Five Star Weekend Cast: Meet the characters and actors of new drama

Friends for... the first time?

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Forcing your friends to be friends always works and never, ever causes conflict. If they all like you and you like all of them they’ll all like each other, right? That’s the goal for Jennifer Garner’s character on the summery new series The Five Star Weekend coming to Sky tonight, so, we’ll see! As for the friends in questions? Here’s everything you need to know about the cast and characters of The Five Star Weekend.

The new series, based on Elin Hilberbrand’s novel, is about a woman in mourning who invites four friends from different periods in her life to spend a perfect weekend on Nantucket with her. There are also some old flames, new love interests, and family members hanging around. It’s a small island, after all.

Jennifer Garner plays Hollis Shaw

Woman with long wavy hair and earrings looking thoughtfully into the distance, with a house in the background.
Peacock

Hollis is a food blogger who organises a girl’s trip to grieve a loss.

From 2001 to 2006, Jennifer starred in Alias as the iconic Sydney Bristow. She didn’t do much television after that, but did appear in the revival season of Party Down recently. Her film credits include, of course, 13 Going on 30, Catch Me If You Can, Juno, Dallas Buyers Club, Pearl Harbor, and Love, Simon. She played the Marvel character Elektra in Daredevil, Elektra, and recently Deadpool & Wolverine.

IG: @jennifer.garner

Chloë Sevigny plays Tatum McKenzie

A woman with long hair wearing a yellow dress sits at a dining table with glasses and flowers.
Peacock

Tatum is Hollis’ childhood best friend.

Chloë is an indie darling and “it girl” with a Golden Globe win for Big Love, an Emmy nomination for Monsters: The Lyle and Erik Menendez Story, and an Academy Award nomination for Boys Don’t Cry under her belt. NBD! You might also know her from films like American Psycho, Kids, Zodiac, Bones and All, After the Hunt, Shattered Glass, and The Last Days of Disco. TV-wise, you may have seen her in American Horror Story: Hotel, Feud: Capote vs. The Swans, The Girl From Plainville, The Mindy Project and Russian Doll.

IG: @chloessevigny

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Regina Hall plays Dru-Ann Jones

Two women looking surprised in a stylish changing room, one in a red blouse and the other in a pink dress.
Peacock

Dru-Ann is Hollis’ college best friend and roommate.

Regina is best known for the Scary Movie franchise, Love & Basketball, Girl’s Trip, One Battle After Another, Support the Girls, and The Hate U Give. She voices Cloud in The Sheep Detectives. She had a recurring role on Ally McBeal, Married, Insecure and Real Husbands of Hollywood. She was in the main cast of Nine Perfect Strangers and the criminally underrated and twisted comedy Black Monday.

IG: @morereginahall

D’Arcy Carden plays Brooke Kirtley

Two women seated at a dining table during an intimate conversation, with elegant table settings and decor.
Peacock

Brooke is Hollis’ motherhood best friend.

D’Arcy is an Emmy nominee for her role as Janet on The Good Place. You may also know her from critical darling Barry or the unfortunately canceled A League of Their Own series. (One of her League costars, Roberta Colindrez, also appears on The Five Star Weekend.) She also showed up at the end of The Handmaid’s Tale, has a recurring role on Nobody Wants This, and was on Broad City back in the day.

IG: @darcycarden

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Gemma Chan plays Gigi Ling

A woman with long dark hair sits at a table, holding a glass of wine, looking thoughtfully to the side.
Peacock

Gigi is Hollis’ new friend.

Gemma is best known for films like Mary Queen of Scots, Crazy Rich Asians, Don’t Worry Darling, Fantastic Beasts and Where To Find Them, Raya and the Last Dragon, and two Marvel movies: Eternals and Captain Marvel. Her television credits include Humans, Secret Diary of a Call Girl, and Watership Down.

IG: @gemmachan

Harlow Jane as Caroline Shaw

A young woman stands next to a red bicycle, looking thoughtfully towards the distance in a garden setting.
Peacock

Caroline is Hollis’ daughter.

Harlow’s previous credits include the 2022 film Dig and the Apple TV+ series High Desert.

IG: @jarlowhane

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Timothy Olyphant plays Jack Finnigan

timothy olyphant in the five star weekend
Peacock//NBC Universal

Jack was Hollis’ first boyfriend.

You know Timothy from long-running shows Justified, Deadwood, and Santa Clarita Diet. He played Rod Reyes on Daisy Jones and the Six. He’s on the new FX series Alien: Earth. His film credits include Live Free or Die Hard, The First Wives Club, and Once Upon A Time in Hollywood. He also plays a fan favorite Star Wars character first introduced on The Mandalorian called Cobb Vanth.

Judy Greer plays Electra

A woman with long blond hair smiles while wearing a blue striped blouse and a scarf, standing outdoors.
Peacock

Per Peacock, Electra is “connected to two characters.” Ominous!

Judy is, of course, Garner’s co-star from 13 Going On 30. You also know her from movies like 27 Dresses, What Women Want, The Wedding Planner, Love & Other Drugs, Adaptation, The Descendants, The Long Walk and shows like Arrested Development, Archer, Two and a Half Men, and The Big Bang Theory.

IG: @missjudygreer

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