Prime Video’s We Were Liars Season 2 Adds Six New Cast Members — Meet the Actors Bringing the 1999 Story to Life

Prime Video is expanding the world of We Were Liars with a major casting update for Season 2, introducing six new series regulars who will play key roles in the story’s highly anticipated flashback timeline. Based on E. Lockhart’s bestselling novels, the series is set to dive deeper into the Sinclair family’s past, particularly the pivotal summer of 1999 that shaped everything.

The new season will follow Cadence’s return to Beechwood Island as she continues to uncover long-buried secrets. At the same time, the narrative will shift into the past, exploring the teenage years of the Sinclair sisters through a fresh cast. This dual timeline structure makes these new additions crucial to the story, as they bring younger versions of key characters to life while introducing new dynamics that expand the mystery.

With production gearing up and anticipation building, here’s a detailed look at all six actors joining We Were Liars Season 2 and the roles they will play.

Josh Dallas as Young Harris

Josh Dallas – Photo Credit – Magnus Hastings

Josh Dallas leads the new additions as Young Harris Sinclair, stepping into a role that represents the patriarch of the powerful Sinclair family in his earlier years. Known for his work on Manifest and Once Upon a Time, Dallas brings a mix of charm and emotional depth that fits the character’s layered personality.

Young Harris is described as charismatic, disciplined, and deeply committed to maintaining the family’s legacy. Despite his success and control over a growing media empire, he lives under the shadow of his more reckless older brother. This internal conflict is expected to play a major role in shaping the Sinclair family’s future, making Harris one of the most important figures in the 1999 storyline.

Dallas’ experience in leading roles positions him well to anchor this part of the narrative. His ability to portray both strength and vulnerability should add complexity to a character who is balancing ambition, family expectations, and personal insecurities.

Costa D’Angelo as Pfeff

Costa_D’Angelo_ by Jonny Marlow

Rising talent Costa D’Angelo joins the cast as Pfeff, a mysterious college student who arrives on Beechwood Island and quickly disrupts the Sinclair sisters’ lives. D’Angelo recently gained attention for his performance in Tell Me Lies, where he played a complex and morally ambiguous character.

Pfeff is described as observant, soulful, and emotionally wounded, traits that make him both intriguing and unpredictable. His presence introduces a new layer of tension to the story, particularly as he becomes entangled in the relationships and secrets that define the Sinclair family.

This role could be a breakout moment for D’Angelo. With his growing filmography and upcoming projects, including high-profile Netflix productions, his casting signals Prime Video’s interest in blending established names with emerging talent.

Parker Lapaine as Young Carrie

Parker Lapaine as Young Carrie

Parker Lapaine takes on the role of Young Carrie Sinclair, a character central to the emotional core of the 1999 storyline. Lapaine has appeared in House of the Dragon and earned praise for her stage performances, showcasing her versatility as an actor.

Young Carrie is portrayed as sensitive, intelligent, and eager for love, embodying the expectations placed on the eldest daughter of a wealthy family. Her life begins to change when a mysterious boy arrives on the island, tempting her with a different future.

This arc suggests a deeply personal journey for Carrie, as she navigates identity, desire, and family pressure. Lapaine’s background in theater could bring a nuanced emotional performance to the role, making her a standout in the ensemble.

Peyton List as Young Tipper

Peyton List Headshot – Credit – Maarten de Boer

Veteran TV actor Peyton List joins as Young Tipper Sinclair, the matriarch figure in her earlier years. With credits spanning Mad Men, The Flash, and Gotham, List brings extensive experience to the role.

Young Tipper is elegant, composed, and highly skilled at managing both social situations and her husband’s ambitions. However, the 1999 timeline reveals cracks beneath this polished exterior. A family crisis forces her to confront her darker side, exposing secrets that could reshape how audiences view her character.

List’s ability to portray complex, morally ambiguous characters makes her a strong fit for Tipper. Her performance is likely to highlight the tension between appearance and reality, a recurring theme in the series.

Elysia Roorbach as Young Penny

Elysia Roorbach- Credit Sam Pickart

Elysia Roorbach plays Young Penny Sinclair, bringing a mix of charm and vulnerability to the role. A graduate of NYU’s Tisch School of the Arts, Roorbach has built her career across theater and screen, including appearances in The Pitt.

Penny is outwardly confident and popular, but beneath her “perfect” image lies a struggle with body image and anxiety. Her storyline in Season 2 will explore these hidden challenges, particularly as someone begins to see through her carefully constructed facade.

This character offers an opportunity to explore mental health themes within the context of a high-society drama. Roorbach’s background in emotionally driven performances could make Penny’s journey one of the most relatable aspects of the season.

Madison Wolfe as Young Bess

Madison Wolfe

Rounding out the new cast is Madison Wolfe as Young Bess Sinclair. Wolfe is known for her roles in The Conjuring 2 and True Detective, where she demonstrated a strong emotional range at a young age.

In the series, Bess is a 16-year-old dreaming of independence and self-expression. She wants to stand apart from her family, particularly her mother, and is eager to fit in with older peers. This desire leads her into risky situations, including choices she may later regret.

Bess’ storyline is expected to capture the intensity of teenage rebellion and identity formation. Wolfe’s experience in both drama and genre projects positions her well to handle the emotional and narrative demands of the role.

What Season 2 Means for the Story

Season 2 of We Were Liars will expand the narrative by weaving together past and present timelines, allowing viewers to understand how the Sinclair family’s secrets were formed. The addition of these six actors is central to that expansion, as they bring the 1999 storyline to life with fresh perspectives and performances.

The series continues under the guidance of showrunners Julie Plec and Carina Adly MacKenzie, both known for their work on character-driven dramas. Their involvement ensures that the new season will maintain the emotional depth and narrative complexity that defined the first installment.

With its blend of mystery, romance, and psychological drama, We Were Liars Season 2 is shaping up to be a deeper and more ambitious continuation of the story. The new cast not only strengthens the ensemble but also opens the door to new themes and conflicts that will keep audiences engaged.

As the Sinclair family’s past begins to unfold, these characters will play a crucial role in revealing the truth. And if the casting is any indication, Prime Video is aiming to make Season 2 an even more compelling chapter in the series.