Role Model recasts image on third album and global tour

Role Model said in an Oct. 16 The Hollywood Reporter interview that his third studio album, released in August, and current global tour extend a looser phase for the 29-year-old singer.

For an artist who previously reached new listeners with Kansas Anymore, his second album, the new cycle tests whether a partly fictional persona can carry songs, staging and a screen role.

“I don’t like anything planned in a show,” Role Model, whose real name is Tucker Harrington Pillsbury, told the publication in a video interview from Los Angeles shortly before Chuck On Tour began in September.

He described concerts as deliberately imperfect rather than tightly choreographed. “People who have been to my shows know this is not a perfect show and there’s nothing planned and there’s nothing perfect about it,” he said.

For the album’s image, Role Model said he moved away from the visual language of Kansas Anymore. “I lost the cowboy boots and I lost the hat, and now it’s just sunglasses and this weird pathetic drunk guy character,” he said.

The character grew out of an unrealised side-project idea, according to the interview. Role Model said he once considered releasing music under the name Chuck Timely and the Hourglass Band without telling his label, then decided the name worked for an album.

The Hollywood Reporter traced his music career to Point Park University in Pittsburgh, where he studied film before encountering students recording songs in dorm rooms. His 2017 song “Cocaine Babe” gained attention on SoundCloud, and his debut EP, Arizona in the Summer, followed the same year.

The interview said the EP later drew Mac Miller’s attention, helping turn Role Model’s early recordings into a professional career that led to a deal with Interscope Records. The article placed Chuck Timely & the Hourglass after three EPs, two earlier albums and viral songs including “Blind” and “Hello!”

Role Model described Kansas Anymore as rooted in Americana influences and said the new album built on that base with yacht-rock keyboards, country guitar tones and Dire Straits-style plucking. Yacht rock refers to polished soft rock associated with late-1970s and early-1980s studio musicianship.

He also said he spent a couple of months assembling a playlist and mood board before making the songs, including references for videos, clothes, sunglasses and album artwork. The preparation helped define the record’s world before production began, he told the publication.

The article also revisited the “Sally” moment from his previous tour, when Jake Shane joined him in Dallas for “Sally, When the Wine Runs Out” three shows into the North American run. Role Model said the guest appearance was not planned and later turned into a recurring fan moment.

Role Model is also preparing for his acting debut in Lena Dunham’s Good Sex, according to the interview. He said Dunham and Natalie Portman helped make his first day on set easier, but the article did not give a release date for the film.

The interview did not provide full tour dates, ticket sales, streaming figures or a release date for Good Sex.

Source: Interview, The Hollywood Reporter, Oct. 16, 2026.