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Cast Overview for ‘The Five Star Weekend’: Jennifer Garner and Timothy Olyphant Come Together Again in New Drama

Cast Overview for 'The Five Star Weekend': Jennifer Garner and Timothy Olyphant Come Together Again in New Drama

Summer Series on Peacock: Five Star Weekend

Peacock has just the right series for a stylish summer by the coast.

Five Star Weekend, inspired by Elin Hilderbrand’s 2023 novel, invites viewers to Nantucket Island. In the story, food blogger Hollis Shaw (Jennifer Garner), who’s coping with her husband Matthew’s death (played by Josh Hamilton), invites three friends from different periods in her life—and a surprising addition—for a special girls’ weekend.

But, despite the luxury and chance for relaxation, unresolved feelings and hidden secrets come to light, challenging Hollis’ simple plans for the gathering.

Warning! Light spoilers ahead for Five Star Weekend, currently streaming on Peacock.

The series features a stellar cast, including Garner, Chloë Sevigny, Regina Hall, D’Arcy Carden, and Gemma Chan, all playing guests at the weekend retreat. Timothy Olyphant will portray Jack, Hollis’ former lover, reuniting with Garner from their prior collaboration in Catch and Release.

Showrunner and executive producer Bekah Branstetter shared that Garner was keen to work with familiar faces for the roles of Matthew and Jack. Garner and Hamilton both appeared in the Apple TV series The Last Thing He Said to Me, while Olyphant and Garner last worked together in a romantic comedy long ago.

Branstetter remarked how wonderful it is to find someone enthusiastic about playing a significant role alongside such a talented female ensemble. “Tim is so generous and charming on set,” she noted, adding that his presence often makes her heart race, akin to old crushes.

If you’re curious about the characters in Five Star Weekend, check out the cast guide and stream the series on Peacock now.

  1. Jennifer Garner as Hollis Shaw

    Hollis Shaw is a food influencer who owns a successful online platform called “Hungry with Hollis.” Following the tragic loss of her husband Matthew, she gathers three friends for a weekend getaway at her Nantucket home.

    Garner is well-known for her roles in Alias, The Last Thing He Said to Me, and films like 13 Going on 30 and Juno.

  2. Chloë Sevigny as Tatum

    Tatum is Hollis’ childhood best friend. They’ve grown apart over the years but share a close bond. While trying to support Hollis, she’s anxious about the heavy news that looms.

    Sevigny is recognized for her roles in Boys Don’t Cry, Big Love, and AHS.

  3. Regina Hall as Druan “Dru” Jones

    Dru, a sports agent, is another of Hollis’ close friends. She feels competitive with Tatum for Hollis’ affection and is dealing with professional challenges that may jeopardize her career.

    Hall is known for her work in the Scary Movie series and Girls Trip.

  4. D’Arcy Carden as Brooke

    Brooke is Hollis’ friend through their children. Struggling to fit in and keep up with the banter, she seeks solace in the Nantucket getaway while grappling with her own personal issues.

    Carden has appeared in The Good Place and The Handmaid’s Tale.

  5. Gemma Chan as Gigi

    Gigi connects with Hollis through social media after the loss of her husband. However, doubts arise among Hollis’ friends about Gigi’s true identity.

    Chan’s notable works include Crazy Rich Asians and Captain Marvel.

  6. Harlow Jane as Caroline “Goose” Shaw

    Caroline, Hollis’ daughter, faces the loss of her father while navigating the trials of friendships and academic responsibilities.

  7. Timothy Olyphant as Jack

    Jack, an ex-lover of Hollis, still resides in Nantucket. Their past relationship brings a mix of nostalgia and tension to the weekend.

  8. David Denman as Kyle

    Kyle, Tatum’s husband, provides support to his wife while she faces challenges during the reunion. He keeps her grounded through the turmoil.

  9. West Duchovny as Aubrey

    Aubrey, Kyle’s daughter, balances her job at a diner with motherhood, all while trying to find her footing in the world.

  10. Josh Hamilton as Matthew Shaw

    Matthew is Hollis’ husband who tragically dies in an accident. His death sets in motion the events of the story, revealing layers of their relationship.

  11. Judy Greer as Electra

    Electra creates conflict between Hollis and Brooke, adding to the already complex dynamics among the group.

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