Source: Entertainment Weekly

The actors — both Emmy winners — starred in the 1999 made-for-TV movie as the cruel Miss Agatha and her wily younger brother Rooster.

The 2025 Emmys have seen a number of touching on-stage reunions thus far — from Alexis Bledel and Lauren Graham taking us back to Stars Hollow with a Gilmore Girls reunion, to Hiroyuki Sanada and Anna Sawai bringing Shogun to the Peacock Theater stage to announce Outstanding Writing for a Drama Series. But no one expected a reunion of two stars of one of the most beloved made-for-TV movies of the 1990s.

Alan Cumming and Kathy Bates took the stage at the 77th Primetime Emmy Awards to present the award for Outstanding Writing for a Variety Series. As they announced as nominees the teams behind Last Week Tonight with John Oliver, The Daily Show, and Saturday Night Live (and presented Oliver’s team with the award), the elder millennials watching at home who grew up on a steady diet of late-’90s TV movies may have realized, This is Miss Agatha Hannigan and her little brother Rooster from Annie!
The pair were a part of the starry cast of ABC’s adaptation of the legendary Broadway musical, which also included Victor Garber, Audra McDonald, Sarah Hyland, and Kristin Chenoweth. Bates played the sadistic owner and operator of the orphanage that provides a home — and not much else — to the titular little orphan (Alicia Morton). Cumming, meanwhile, played Miss Agatha’s troublemaker younger brother, Daniel Francis, also called “Rooster.”

In truth, Cumming actually played two roles, as his character is hired by his sister to go in disguise as Ralph Mudge, who falsely claims to be Annie’s father.

Both Bates and Cumming were nominated at the 2025 Emmy Awards and their counterpart, the Creative Arts Emmys. Bates for her performance as Madeline “Matty” Matlock in CBS’ new twist on the classic legal drama Matlock, and Cumming for both Outstanding Host for a Reality or Reality Competition Program for The Traitors, and as a member of the Traitors crew for Outstanding Reality Competition Program.

Cumming won both of his awards, while Bates lost to Severance star Britt Lower.

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