2006–2017: Breakthrough and acclaim
After being voted Best Supporting Actress for Gone Baby Gone by the National Board of Review, as well as the critics circles in New York, Los Angeles, Boston, San Francisco and Washington, D.C., Ryan's performance was also nominated for a Golden Globe Award, a Screen Actors Guild Award, and an Oscar for Best Performance by an Actress in a Supporting role at the 80th Academy Awards.
Ryan appeared in Changeling (2008), directed by Clint Eastwood, and opposite Matt Damon in Paul Greengrass's Green Zone (2010). In September 2010, she completed filming a role in Philip Seymour Hoffman's directorial film debut, Jack Goes Boating, taking over the role of Connie originally played by Beth Cole in the stage version. Ryan received strong notices for her performance in Tom McCarthy's Win Win the next year, winning Best Supporting Actress awards from multiple regional critics groups. She appeared in a six-episode arc on The Office as dorky HR rep Holly Flax. She reprised her role on The Office in seasons 5 and 7. Ryan joined the cast of HBO's In Treatment for its third season in 2010, playing the therapist of Dr. Paul Weston.
Ryan was a part of the core ensemble of the 2014 Best Picture Academy Award winning film Birdman, sharing in the cast's Screen Actors Guild Award for Outstanding Performance by a Cast in a Motion Picture victory. In 2015, she starred as Mary Donovan opposite Tom Hanks in the film Bridge of Spies, and reunited with her In Treatment co-star Gabriel Byrne in Louder Than Bombs, the English-language debut of Joachim Trier. Early the next year, Ryan was cast as Tracy, her first on-screen leading role, in Abundant Acreage Available, a rural family drama from Junebug screenwriter Angus MacLachlan. Upon the film's premiere at the 2017 Tribeca Film Festival, Ryan drew universal acclaim for her performance, with The Wrap noting that she "holds the screen no matter what she's doing and who she's with" and Flavorwire raving that Ryan "sounds notes that are quietly dazzling in their complexity." Variety chief film critic Peter Debruge dubbed the performance a career highlight:
It's a pleasure to see such a fine actress navigate the nuances of her role ... Only on the big screen are we able to fully appreciate the minutely detailed nature of Ryan's performance, revealing Tracy's soul via the slightest narrowing of the eyes or the almost-subliminal tensing of her cheekbones. As we know, Junebug earned Amy Adams an Oscar nomination, and if the world were fair, this role would bring another Amy similar attention.
Ryan received some of the best reviews of her career for her leading role in the Roundabout Theater Company's 2016 production of Love, Love, Love. Ben Brantley of The New York Times praised her "smashing comic performance," The Hollywood Reporter called her work "emotionally vital," and The Associated Press raved that "Ryan is absolutely magnetic ... nailing her charming, unpredictable character with perfect comedic timing." In an article exploring various famous actresses working on the stage, The Washington Post theater critic Peter Marks highlighted Ryan's work in the play:
The revelation is not that Amy Ryan is good. It's that she's this good ... Ryan, whose range has been apparent for years, in dramatic performances nominated for Tonys (Uncle Vanya) and Oscars (Gone Baby Gone), as well as in nuanced comic turns on television shows like The Office, manages a feat in Love, Love, Love that she's never accomplished so fluidly before: taking charge. She delivers a front-and-center performance of such beguiling dynamism (in a thoroughly convincing English accent) that you feel this Roundabout Theatre Company production has done for her precisely what was intended. It exposes a new facet of her talent — and leaves us with that uplifting itch, to be there the next time she's on a stage.
For her performance in Love, Love, Love, Ryan won the Obie Award for Distinguished Performance by an Actress, and was nominated for the Drama Desk Award for Outstanding Actress in a Play and the Drama League Award for Distinguished Performance.