The Daddies' music is primarily a mix of swing and ska, contrastingly encompassing both traditional jazz-influenced variations of the genres as well as contemporary rock and punk hybrids, characterized by a prominent horn section and Perry's acerbic and innuendo-laced lyricism often concerning dark or political subject matter.

Initially drawing both acclaim and controversy as a preeminent regional band, the Daddies gained wider recognition touring nationally within the American ska scene before ultimately breaking into the musical mainstream with their 1997 swing compilation Zoot Suit Riot.

Released at the peak of the 1990s swing revival, Zoot Suit Riot sold over two million copies in the United States while its eponymous single became a radio hit, launching the Daddies to the forefront of the neo-swing movement.

Sharing similar musical ambitions and a mutual disinterest in school, the pair agreed to drop out of college together and start a band, forming the punk trio The Jazz Greats in 1983, which evolved into the Paisley Underground-styled garage rock group Saint Huck, which lasted from 1984 to 1987.

[3][4] As the rise of grunge began to phase punk and hardcore out of the Northwest underground by the late 1980s, Perry set out to start a band that stood in defiant contrast to the shoegazing attitude of alternative rock, showcasing high energy dance music and Zappa-esque theatricality in an attempt to create something that an audience would react to viscerally instead of passively.

[5][6][7] Recruiting a horn section led by alto saxophonist Brooks Brown, Perry and Schmid formed their latest band Mr. Wiggles – named so after a Parliament song – in November 1988, playing their first show in Springfield as part of a benefit concert for workers of the Nicolai door manufacturing plant, who were then engaged in a union strike.

[4][5][8][9] "My conception of punk", Perry told The Rocket, "was doing whatever the hell you wanted as long as it had vitality and wasn't overly stupid ... something exploratory and experimental", citing influence from genre-bending bands such as The Clash and the Meat Puppets.

[16] Fusing punk rock and jazz horns with funk grooves, Ferociously Stoned drew favorable critical comparisons to contemporaries Faith No More and the Red Hot Chili Peppers while also becoming a regional best seller.

[33] Distributed by noted indie label Caroline Records, Kids on the Street wound up becoming the Daddies' most successful release at the time, staying on The Rocket's Retail Sales Top Twenty for over seven months and even working its way onto Rolling Stone's Alternative Charts.

[6][45][46][47] The result, Zoot Suit Riot: The Swingin' Hits of the Cherry Poppin' Daddies, became an unexpectedly popular item as the band went on tour, reportedly selling as many as 4,000 copies a week through their Northwest distributors.

[6] While stopped in Los Angeles during another tour together, Reel Big Fish arranged a meeting between their label Mojo Records and the Daddies in the hopes of helping the band obtain a distribution deal for Zoot Suit Riot.

[8][43][46] Mojo nevertheless persisted, and much to the band's surprise, "Zoot Suit Riot" soon found regular rotation on stations such as Los Angeles' influential KROQ-FM, helping establish swing music in the mainstream and leading to its eventual commercial breakthrough, with the Daddies at the forefront.

[53] By this time, the group's touring conditions had greatly improved, thus enticing Dan Schmid – who had originally left the band due to health concerns – to return as the Daddies' bassist at Perry's request.

[54] Although the Daddies were experiencing commercial success under the guise of swing revivalists, having been declared the "leaders" of the movement by Rolling Stone, the band openly contested being labeled a retro act at the exclusion of their dominant ska and punk influences and modernist lyricism.

During the height of the Daddies' popularity, Perry found the band's mainstream notoriety was causing an alienating effect on his personal life, claiming it to have negatively changed his relationships with friends and even subjected him to occasional heckling from strangers who recognized him in public.

A loose concept album reflecting Perry's disillusionment over the cultural zeitgeist and his experience with fame - as he described it, a "bittersweet" record about "being alienated and hoping to connect"[61] - Soul Caddy marked a continuation of the band's musically varied format, intended to introduce a truer perspective of the Daddies' sound and personality to both their swing-based fans and a wider audience.

[73] Some reviewers chastised the band for what was being seen as an abandonment of their swing "roots" in favor of a trendier sound,[74] while a few criticized the Daddies' entire musical aesthetic — UGO's Hip Online stated bluntly, "covering five or six genres on one album is just insane".

[76] Despite some moderate critical praise including a glowing review from AllMusic, who called the album's "impressively surprising" array of sounds "refreshing coming from a band who was assumed to be generic retro swing",[77] Soul Caddy failed to achieve the chart success or commercial attention of its predecessor.

Drummer Tim Donahue, after a stint with The Visible Men, worked as a session musician, recording on albums for artists including TobyMac and Shawn McDonald and playing in Yngwie Malmsteen's band for his 2001 European tour.

[65][82] Following four years of relative inactivity as the band maintained their relaxed touring pace, Perry began writing material for a new Daddies album in early 2006, claiming to have come to the realization of a cathartic reliance on songwriting.

[89] Skaboy JFK was released in September 2009 to a largely positive critical reception, followed by further touring into 2010, taking the Daddies back across Europe and the United States, as well as appearing alongside Fishbone and The Black Seeds at the 11th Victoria Ska Fest in British Columbia, where the band played the first all-ska set of their career.

[96][97] On June 20, 2012, the Daddies launched a PledgeMusic campaign to help finance the final stages of the album's production, successfully reaching its target on August 14 and continuing to collect pledges into the following year, ultimately raising 133% of its goal.

[106] Over the next four years, Perry gave sporadic updates on Twitter and in interviews on the development of this new album of originals, describing it in 2016 as "a little like Ferociously Stoned 2", featuring a primary emphasis on rock and funk, and then later in 2017 as "swing-ska-rockabilly-psychobilly".

[119] This started with the single and video release of "Platform Shoes", another glam rock-styled song from the deluxe edition of White Teeth, Black Thoughts, in mid-March and a cover of Canadian rock band The Kings' 1980 hit "Switchin' to Glide" in mid-May.

The Daddies are generally classified as a swing and/or ska band by the media, and their music is largely composed of various interpretations of both genres, ranging from traditional jazz and big band-influenced forms to modernized rock and punk fusions.

[123] The Pacific Northwest Inlander wrote of this style in 1994, "atop the swing of the band's jazz you can hear strains of Parliament-Funkadelic, crumbs of barrelhouse rhythm and blues, snippets of ska, and huge whiffs of in-your-face punk rock", likening the Daddies to "Cab Calloway-meets-Johnny Rotten, or the Duke Ellington Orchestra pumped up on steroids and caffeine".

[10][61][137][138] Steve Perry is the Daddies' sole lyricist, and writes the majority of his songs in a fictional narrative format he credits as being influenced by Randy Newman, Ray Davies and Jarvis Cocker, often told about or through the unreliable perspective of downtrodden characters struggling against adversity.

[17][19][38] Perry often incorporates commentary on contemporary American politics into his music, such as addressing issues relating to the financial crisis of 2007–2008 on 2013's White Teeth, Black Thoughts and exploring themes of race and class during the Donald Trump administration on 2019's Bigger Life.

[142] The Daddies have often been criticized for their seeming juxtaposition of lurid subject matter and profanity with jazz and swing music,[143][144] though Perry has defended the band's predilection towards "darker" lyricism and visuals, calling to attention his interest in the era's film noir and avant-garde artistic movements.

[3][48] Although the Daddies have been cited as an influence on ska punk bands the Mad Caddies and Spring Heeled Jack U.S.,[153][154] SF Weekly once claimed the group has "never gotten the accolades it deserves" for their eclectic funk-ska repertoire.