Set against the backdrop of 1930s Hollywood, we follow the story of Phil Stern, the brilliant agent portrayed by Steve Carell, who stands as a titan in the entertainment industry. Our narrative kicks off at a lively party, where Phil unexpectedly receives a call he assumes is from the iconic Ginger Rogers. However, the truth unfolds when it’s his sister, Rose Dorfman (played by Jeannie Berlin), informing him that her son will be moving to Los Angeles to work with him.
Bobby Dorfman, played by Jesse Eisenberg, is a young man who shares a home with his mother Rose and father Marty (Ken Stott), a jeweler. Bobby's family is rounded out with two siblings: the schoolteacher Evelyn (Sari Lennick), who is married to Leonard (Stephen Kunken) and has a daughter, and Ben (Corey Stoll), a notorious gangster known for his violent dealings and numerous murders in the area.
As Bobby embarks on his journey to Hollywood, he faces an uphill battle. His attempt to meet Phil at his office results in a long wait, only to discover Phil has jetted off to Mexico with his wife. Feeling disheartened one night, Bobby orders a woman, Candy (Anna Camp), to his apartment. Mistakenly, she arrives at the wrong room, and after a confrontation that leads to her tears, Bobby reluctantly shares the intimate moment before sending her away.
Finally gaining Phil's attention, Bobby's dreams seem to align when Phil agrees to take him under his wing. He’s introduced to Vonnie (Kristen Stewart), a kind-hearted secretary who shows him around the glitz of Hollywood, including celebrity homes like Joan Crawford’s. Bobby becomes infatuated with Vonnie’s charming personality, but soon discovers she is entangled with a journalist named Doug—who is revealed as Phil himself. Caught in a web of love and deception, Vonnie struggles with her feelings for Phil while trying to maintain her dignity.
As Bobby’s relationship with Vonnie blossoms following her split with Phil, complications arise when Phil's jealousy bubbles over. Phil, unable to cope with losing Vonnie, confides in Bobby about his affair without revealing the identity of his partner. One fateful day, Phil proposes to Vonnie, leaving Bobby heartbroken when he discovers she chooses Phil over him.
Resigning himself, Bobby heads back to New York City to help his gangster brother Ben run a nightclub, where he soon gets acquainted with the high society of the era. During this time, he meets Veronica Hayes (Blake Lively), a recent divorcee, and their whirlwind romance leads to a hurried marriage after an unexpected pregnancy.
Amid family drama sparked by neighborly disputes involving Ben’s violent tendencies—culminating in a murder that lands him in the electric chair—Bobby finds himself navigating through grief and moral dilemmas. As the club gains notoriety after Ben's execution, Bobby’s past resurfaces when Phil and Vonnie visit New York, rekindling unresolved feelings during a nostalgic day out.
The story culminates on New Year’s Eve, as both Bobby and Vonnie, now in different lives, reflect on lost opportunities and unfulfilled desires. Each of them, surrounded by festivities, find themselves engulfed in sadness and regret as the countdown to midnight echoes in their hearts.
