Prime Video has announced six new series regulars joining We Were Liars season 2 as the drama expands its narrative scope to explore the Sinclair family’s dark secrets from the summer of 1999. The casting additions include Josh Dallas, Costa D’Angelo, Parker Lapaine, Peyton List, Elysia Roorbach, and Madison Wolfe, who will portray younger versions of established characters alongside introducing new figures into the wealthy family’s complicated history.
The second season will adapt E. Lockhart’s 2022 prequel novel Family of Liars while continuing present-day storylines featuring Emily Alyn Lind as Cadence. According to the season two logline, Cadence returns to Beechwood Island to confront her truth and uncover family secrets, discovering that the summer of 1999 was marked by first love, rivalry, and murder.
The flashback structure allows the series to explore how the Sinclair sisters became the complicated adults viewers met in season one while maintaining narrative momentum in the present timeline. Production is set to begin this summer with a likely 2027 release date. Here’s a breakdown of each new cast member and the character they’ll bring to life in this Kennedy-esque dynasty’s troubled past.
1. Josh Dallas as Young Harris Sinclair
Josh Dallas brings a substantial television pedigree to We Were Liars through his starring roles in two major network series. Most recently, Dallas led NBC’s Manifest as Ben Stone across four seasons, with the show becoming what Variety called “the undisputed breakout of the 2019 season” before moving to Netflix for its final episodes. Prior to Manifest, Dallas spent seven seasons playing Prince Charming on ABC’s Once Upon a Time, establishing himself as a reliable leading man in fantasy-driven storytelling.
His feature film credits include playing Fandral in Marvel’s Thor, appearing in Anthony Hemingway’s Red Tails, and voicing characters in Disney’s Zootopia and its sequel. Dallas is represented by Verve, Untitled Entertainment, and Gendler, Kelly & Cunningham.
In We Were Liars season 2, Dallas steps into the role originated by David Morse, playing a younger version of Harris Sinclair. The character description reveals Harris as charming, well-heeled, and dedicated to raising his daughters to honor the family name. Despite commanding a media empire, Harris finds himself perpetually cast in the shadow of his older brother, who is more charismatic but far more reckless. This dynamic creates tension as Harris envisions a specific future that his brother’s behavior threatens to derail. The role allows Dallas to explore the formative years of a patriarch whose stoicism in crisis masks deeper family conflicts that will reverberate for decades.
2. Costa D’Angelo as Pfeff
Costa D’Angelo represents one of the most exciting emerging talents in the cast, having recently delivered a breakout performance in Hulu’s Tell Me Lies. In that series, he portrayed a complex psychology graduate student who moonlights as a drug dealer and shares a tangled past with central characters. His character’s romantic involvement with Lucy, played by Grace Van Patten, added significant tension to the show’s layered relationship dynamics.
The Australian actor trained at one of his country’s leading arts institutions before building momentum across domestic and international projects. He first gained recognition on the long-running Australian series Neighbours before expanding his presence with appearances in Crazy Fun Park on ABC and feature projects including The Deb (2024) and Shiver (2026). D’Angelo is currently filming a Netflix hockey series alongside Michelle Monaghan, produced by Shawn Levy with Trey Edwards directing. He also appears in Zoe Kazan’s highly anticipated adaptation of East of Eden for Netflix, premiering this fall. He is represented by Entertainment 360, Shanahan Management, and Jackoway Austen Tyerman.
D’Angelo’s character Pfeff is described as a New England college kid with a mysterious edge who arrives on Beechwood Island without intending to upend the Sinclair sisters’ lives, though doing so becomes inevitable. The character is observant, soulful, and wounded in what Prime Video describes as “the most compelling way.” This suggests Pfeff will serve as a catalyst for the dramatic events of summer 1999, potentially representing the “intriguing new boy” who tempts Carrie toward a different future.
3. Parker Lapaine as Young Carrie Sinclair
Parker Lapaine brings stage and screen credentials to the role of young Carrie Sinclair, the character originated by Mamie Gummer in season one. Lapaine recently received rave reviews on the UK stage for her performance in Red Speedo, directed by acclaimed director Matthew Dunster and performed opposite Cole Finn. Her television work includes appearing in the final episode of House of the Dragon season 2, demonstrating her ability to handle high-profile fantasy drama.
Lapaine is represented by Atlas Artists and Hamilton Hodell, agencies known for representing talented performers working across British and international productions.
Her character Carrie is described as sensitive, quick-witted, and yearning to be loved in the summer of 1999. Ostensibly the Harvard-bound, well-heeled, obedient eldest daughter, Carrie’s carefully constructed life changes when an intriguing new boy arrives on the island and tempts her with a very different kind of future. This characterization suggests Carrie’s teenage years contained more rebellion and romantic complexity than her adult persona reveals, with decisions made during this formative summer potentially explaining the guarded woman she becomes.
4. Peyton List as Young Tipper Taft Sinclair
Peyton List brings extensive television experience spanning network, cable, and streaming platforms to the role of young Tipper Taft Sinclair, originally portrayed by Wendy Crewson. List’s recent work includes recurring roles on Star Trek: Picard and ABC’s The Rookie, adding to an impressive resume that demonstrates her versatility across genres.
Her previous recurring roles include playing Poison Ivy on Fox’s Gotham, appearing on CW’s Charmed, and starring in USA’s Colony, with both Gotham and Colony wanting to promote her to series regular status. List also held lead series regular positions on CW’s Frequency and The Tomorrow People, ABC’s Flash Forward and Big Shots, and appeared as Lisa Snart (the Golden Glider) on The Flash. Perhaps most notably, she recurred across five seasons of AMC’s critically acclaimed Mad Men as Jane Sterling, demonstrating her ability to navigate complex period drama. She recently appeared in the independent film Spinning Gold directed by Tim Bogart. List is represented by Innovative Artists and Schreck Rose Dapello Adams Berlin & Dunham.
The character description reveals Tipper as the young matriarch of a Kennedy-esque dynasty who can bake perfect pies, host exceptional dinner parties, and deftly pull strings in her husband’s quest for wealth and power. She has always accomplished everything with effortless grace and old-money elegance, but the summer of 1999 brings a family crisis that exposes her sharp edges, icy temper, and dirty secrets. This suggests Tipper’s carefully cultivated persona cracks under pressure, revealing the calculating and potentially ruthless woman beneath the gracious hostess facade.
5. Elysia Roorbach as Young Penny Sinclair
Elysia Roorbach holds a BFA in Drama from NYU’s Tisch School of the Arts, where she studied at Atlantic Acting Company and Stonestreet Studios, including a term at London’s Royal Academy of Dramatic Art. Immediately upon graduating, she starred in the world premiere of Las Aventuras de Juan Planchard, a co-production between Tectonic Theater Company and Miami New Drama directed by Tony Award nominee and Presidential Medal of Arts recipient Moisés Kaufman.
Her theater credentials continued with starring as Honey in South Coast Repertory’s production of Who’s Afraid of Virginia Woolf, one of American theater’s most demanding roles. Roorbach has appeared in over a dozen short films with successful festival runs and can be seen recurring in season 2 of HBO Max’s Emmy Award-winning series The Pitt. She is represented by Realm Talent and Schreck Rose Dapello & Adams.
Roorbach takes over the role of Penny Sinclair from Caitlin FitzGerald, playing the character during her teenage years. The character description reveals Penny as charming, popular, and a hopeless romantic with a competitive streak “a mile wide.” However, beneath her “Perfect Penny” mask, she struggles with body image issues and a burgeoning panic disorder that she keeps hidden from everyone until someone unexpected sees beyond her facade. This vulnerability suggests Penny’s adult perfectionism stems from teenage insecurities and mental health challenges that were never properly addressed, creating patterns that persist into adulthood.
6. Madison Wolfe as Young Bess Sinclair
Madison Wolfe brings the most extensive young actor credentials to We Were Liars, having worked consistently since childhood with acclaimed directors and in high-profile projects. Most recently, she starred in Netflix’s The Hunting Wives opposite Brittany Snow, Malin Åkerman, and Chrissy Metz, and appeared in AMC’s Anne Rice’s Mayfair Witches.
Wolfe is known for playing Woody Harrelson’s daughter on HBO’s True Detective and appearing in The Campaign opposite Will Ferrell. Her horror credentials include starring in James Wan’s The Conjuring 2 and the feature film I Kill Giants opposite Zoe Saldaña. She has worked with acclaimed directors David O. Russell in Joy and Jay Roach in Trumbo, appearing alongside Bryan Cranston, Diane Lane, Elle Fanning, Helen Mirren, and John Goodman. Wolfe is represented by Untitled Entertainment and UTA.
She takes on the role of young Bess Sinclair, originally played by Candice King. The summer she turns 16, Bess dreams of being a songwriter and adventurer, and most importantly, nothing like her mother. Desperate to fit in with older kids, especially three college-age boys who have unexpectedly moved into the guest house, Bess will do anything to impress them, including some things she’ll live to regret. This characterization positions Bess as potentially the most vulnerable Sinclair sister, whose desire for acceptance leads to decisions with long-lasting consequences.
What This Means for We Were Liars Season 2
The casting announcements confirm that We Were Liars season 2 will operate on dual timelines, with present-day Cadence’s investigation into family secrets intercut with extensive flashbacks to summer 1999. This structure allows the show to explore how the Sinclair family’s dysfunction developed while maintaining narrative momentum in the present.
Author E. Lockhart confirmed to The Hollywood Reporter that viewers will still see Cadence, Johnny, and the adult sisters, but the prequel storyline from her novel Family of Liars will receive substantial attention. The showrunners are “cooking up new stories” that expand beyond the source material while honoring its themes.
The mention of “even murder” in the season two logline suggests the 1999 flashbacks will reveal dark secrets far beyond typical family drama, potentially explaining the psychological damage and complicated relationships that define the Sinclair family in the present day.
We Were Liars season 2 is written and executive produced by co-showrunners Julie Plec (The Vampire Diaries, Legacies) and Carina Adly MacKenzie (Roswell, New Mexico, The Originals). Also executive producing are Emily Cummins for My So-Called Company, Brett Matthews, Marguerite MacIntyre, and E. Lockhart. Universal Television and Amazon MGM Studios are behind the project.