structural:scholar_edition
2015–2019

On January 14, 2015, Amazon Studios announced a full-season order for a half-hour Amazon Prime Instant Video series that Allen would write and direct, marking the first time he has developed a television show. Allen said of the series, "I don't know how I got into this. I have no ideas and I'm not sure where to begin. My guess is that Roy Price will regret this." At the 2015 Cannes Film Festival, Allen said of his upcoming Amazon show: "It was a catastrophic mistake. I don't know what I'm doing. I'm floundering. I expect this to be a cosmic embarrassment." On September 30, 2016, Amazon Video debuted Allen's first television series production, Crisis in Six Scenes. The series is a comedy set during the 1960s. It focuses on the life of a suburban family after a surprise visitor creates chaos among them. It stars Allen, Elaine May, and Miley Cyrus, with the latter playing a radical hippie fugitive who sells marijuana.

Allen's next film, Café Society, starred an ensemble cast, including Jesse Eisenberg, Kristen Stewart, and Blake Lively. Bruce Willis was set to co-star, but was replaced by Steve Carell during filming. The film is distributed by Amazon Studios, and opened the 2016 Cannes Film Festival on May 11, 2016, the third time Allen has opened the festival. Peter Bradshaw of The Guardian gave the film a positive review, writing, "The film looks ravishing, with shots of New York which recall images in Allen's great work, Manhattan, but however wonderfully composed, there is something almost touristy in both them, and in his evocation of golden age Tinseltown, like his homages to Paris and Rome. Allen brings it all together in his closing moments which conjure something unexpectedly melancholy and shrewdly judged. It has entertainment and charm."

In September 2016 Allen started filming the drama film Wonder Wheel, set in the 1950s in Coney Island, and starring Kate Winslet, Justin Timberlake, Juno Temple, and Jim Belushi. The film served as the closing night selection at the 55th New York Film Festival on October 15, 2017, and was theatrically released on December 1, 2017, as the first movie self-distributed to theaters by Amazon Studios. The film received mixed reviews, with critics praising Winslet's leading performance. Owen Gleiberman of Variety wrote, " Wonder Wheel isn't a comedy—on the contrary, it often feels like the most earnest kitchen-sink drama that Clifford Odets never wrote. It may or may not turn out to be an awards picture, but it's a good night out, and that's not nothing." In 2017, Allen received a standing ovation when he made a rare public appearance at the 45th Annual Life Achievement Tribute award ceremony for Diane Keaton. Before presenting her with the award he spoke about their longtime collaboration and friendship, saying, "From the minute I met her, she was a great, great inspiration to me. Much of what I have accomplished in my life I owe for sure to her".

Allen returned to filming in New York City with the romantic film A Rainy Day in New York, starring Timothée Chalamet, Selena Gomez, Elle Fanning, Jude Law, Diego Luna, Liev Schreiber and Rebecca Hall. The production in New York began in September 2017. During the film's release, Chalamet, Gomez, and Hall announced, in the light of the Me Too movement, that they would donate their salaries to various charities. The film received mixed reviews but earned praise for its performances. In February 2019 it was announced that Amazon Studios had dropped A Rainy Day in New York and would no longer finance, produce, or distribute films with Allen. He filed a lawsuit for $68 million, alleging Amazon gave "vague reasons" to terminate the contract, dropped the film over "a 25-year old, baseless allegation", and did not make payments. The case was later settled and dismissed. It was released throughout Europe beginning in July 2019, receiving mixed reviews and grossing $20 million. After over a year's delay, the film was released in the U.S. on October 9, 2020, by MPI Media Group and Signature Entertainment.

In May 2019, it was announced that Allen's next film would be titled Rifkin's Festival, and Variety magazine confirmed that its cast would include Christoph Waltz, Elena Anaya, Louis Garrel, Gina Gershon, Sergi López, and Wallace Shawn, and that it would be produced by Gravier Productions. The film was produced with Mediapro, an independent Spanish TV-film company. Rifkin's Festival completed filming in October 2019. On September 18, 2020, it premiered at the San Sebastián International Film Festival. It received mixed reviews, though Jessica Kiang of The New York Times called it "to the ravenous captive, like finding an unexpected stash of dessert".