381 – Happy Endings

After the edgy sexual comedy The Opposite of Sex made Don Roos a hot indie name and the drowsy romance of Bouncedampened the vibe, Roos returned in 2005 with ensemble dramedy Happy Endings. With a cast of Lisa Kudrow, Steve Coogan, and Laura Dern, the film looks at the secrets and sexual boundaries of a group of Los Angelenos. But it was the wayward and musical performance by Maggie Gyllenhaal that earned the biggest raves and an Independent Spirit Award nomination.

This episode, we talk about Gyllenhaal’s road to her first nomination for Crazy Heart and she joins our Six Timers Club. We also talk about Kudrow’s upcoming return in The Comeback, Tom Arnold’s critically praised performance, and the film being released in the same summer as LA ensemble Best Picture winner, Crash.

Topics also include Dern in the TEN Timers Club, aughts-y onscreen homophobia, and The Bride!.

374 – Booksmart

Happy New Year, Garys! We’re kicking off 2026 with something more bubbly and light-hearted, 2019’s Booksmart. Sold as an ultra-modern and female take on boy-led high school raunch comedies, the film stars Kaitlyn Dever and Beanie Feldstein as best friends who decide to live it up after spending their entire high school experience stuck in books. After debuting at SXSW, the film generated a mountain of discussion that yielded disappointing box office results, but managed to stick around in the precursor race until the last minute.

This episode, we talk about the film’s delightful ensemble of faces of the future and Olivia Wilde’s debut directing duties that earned her a number of first film prizes that season. We also talk about Feldstein’s drubbing during the Funny Girl run on Broadway, Dever joins our Six Timers Club, and the shadow of Lady Bird unfairly set expectations for this film.

Topics also include Forte vs. Arnett, the 2019 Globe Musical/Comedy Best Actress nominees, and “I wish you luck with your trees.”

365 – Hanging Up

We were heartbroken at the news of Diane Keaton’s passing, so we decided to quickly get another of her films in the THOB books. Keaton’s final directorial effort was Hanging Up, based on Delia Ephron’s fictionalized experience coping with distant sisters during the final years of their father’s life. Co-written by Delia and Nora Ephron, Meg Ryan took the lead with Keaton and Lisa Kudrow starring as the sisters and Walter Mathau as the aging father. Originally intended for a 1999 release, the film was received harshly by critics when it was ultimately released in 2000.

This episode, we talk about the behind-the-scenes tensions that played out onscreen and the unfavored collaborations between the Ephron sisters. We also talk about our favorite Keaton performances, Kudrow’s critical success with The Opposite of Sex, and Lisa Schwarzbaum F score reviews.

Topics also include Diet Coke commercials, Everything is Copy, and Keaton tributes.