For most listeners, even devoted pop music fans, Rupert Holmes is known for one thing: the perennial camp classic "Escape (The Piña Colada Song)," the quintessential distillation of the high-flying, hedonistic, swinging late '70s. It so thoroughly captured the sound and attitude of its time that it pegged Holmes as not just a one-hit wonder, but a one-trick pony, a laid-back singer/songwriter who could only chronicle tales of love and loss, often in a cornball fashion. But like Randy Newman, who for a while was pegged as a novelty songwriter or midget bigot for his fluke hit of "Short People," "Escape (The Piña Colada Song)" was a misinterpreted piece of satire, and it did not come close to representing the breadth, scope, or intent of Rupert Holmes' work. Unlike Newman, who was an acclaimed and well-respected songwriter prior to "Short People" and found his reputation relatively quickly restored afterward through his subsequent albums and work as a film composer, Holmes has never been critically rehabilitated, although he has one of the more interesting careers on the fringe of pop music. Before "Escape" he had a number of idiosyncratic orchestral pop albums, pitched somewhere between Harry Nilsson, Jimmy Webb, and Brian Wilson, produced and written for Barbra Streisand. After he ditched his pop music career in the early '80s, he turned to Broadway, winning Tonys for his score for the The Mystery of Edwin Drood, before writing a series of mystery plays, adapting musicals for the stage and, finally, authoring novels, the first of which was turned into a film starring Kevin Bacon and Colin Firth by the acclaimed director Atom Egoyan.
Clearly, Holmes had far more to offer than "The Piña Colada Song," but it'd be easy for even those pop fans to think otherwise since apart from his debut Widescreen and his 1979 hit Partners in Crime, his albums never hit CD and were out of print for decades. Hip-O Select's exhaustive and immensely enjoyable box set Cast of Characters: The Rupert Holmes Songbook, containing all of eight of his studio albums and a disc of rarities, goes a long way to restoring his reputation, offering an argument that he's an intriguing '70s pop eccentric, not a predictable MOR hack. Granted, he's mildly eccentric, not nearly as odd as Newman, Nilsson, Webb or Wilson, nor is he an innovator like that quartet. Instead, Holmes is pop formalist, working within accepted conventions and offering quirky, witty takes on familiar sounds and themes. These are skills that served him well later as a mystery novelist, but they also made his pop records, particularly those recorded during the '70s, quite fascinating from both musical and lyrical standpoints.
Holmes' strangest record was his first, 1974's Widescreen, an album-long tribute to the silver screen that was appropriately cinematic in scope and indebted to Randy Newman's incorporation of Hollywood music in his own songs. An ambitious, far-reaching affair beginning with the lush title track and ending with a ten-minute radio play called Psycho Drama, it wasn't a commercial success, but his meticulous, tasteful songcraft earned the attention of Barbra Streisand, who not only covered the album's "Widescreen" and "Letters That Cross in the Mail" for her 1975 LP Lazy Afternoon, but hired Holmes to produce the album as well. This was enough to loosen him up for his eponymous 1975 album, a loose, funny, tremendously appealing album whose wit was at times reminiscent of Harry Nilsson's -- particularly in how he quoted several Beatles tunes in "I Don't Want to Hold Your Hand" (à la Nilsson's wonderful "You Can't Do That"), or how he planted his tongue firmly in his cheek for the islands anthem "Rifles and Rum" or "Everything's Better When You're Drunk." On his next effort, 1977's Singles, he was deliberately gunning for a hit single, so he tried a little bit of everything, from smooth MOR ballads and pop such as the catchy "I Don't Want to Get Over You" (later covered by Mac Davis) to the laid-back soulful pop of "Who, What, When Were, Why" (later recorded by both Dionne Warwick and Manhattan Transfer) and the glorious, surprisingly hard-rocking "Aw Shucks." It wasn't a hit, but it paved the way for 1978's Pursuit of Happiness, which was caught halfway between Holmes' intent to craft a concept album about a small town and his label's desire for a genuine hit single that Singles didn't deliver. It's muddled, but not a bad album, thanks to both his more introspective tunes -- plus oddities like "Guitars," which is arranged for an army of acoustic guitars -- and his chart-oriented popcraft (which is not far removed from Boz Scaggs) and it did have his first charting single with "Let's Get Crazy Tonight," which pointed in the direction of "Escape," his first genuine hit and the first song on 1979's Partners in Crime. Not only did that album have commercial success, but it was the perfect blend of Holmes' wit and songcraft, where the glossy production enhanced his wry satire.
After Partners in Crime, Holmes' recorded work started to slip. Its 1980 follow-up Adventure was written and recorded quickly; it's sonically similar to Partners, but it's neither as cohesive thematically, or as successful on a track-by-track basis. A year later, he delivered Full Circle, an awkward fusion of his early-'80s soft rock and the cinematic sprawl of Widescreen, and then he slowly slid away from pop, turning his attention elsewhere -- namely the stage and novels. He recorded a comeback album called Scenario in 1994 for JVC in Japan, and while it never was released in the States, it's a thoroughly charming collection of low-key, subtle tunes.
Hearing all these albums in this five-disc box set, it's easier to take the post-Partners in Crime slide in stride -- while Adventure and Full Circle are uneven, they are enjoyable, and their best moments can stand alongside his '70s work (Holmes' own album-by-album liner notes also help put the records in context). Similarly, the fifth disc of rarities, while playing as a clearinghouse of odds-and-ends, has plenty of terrific moments, including original demos of songs he wrote for Streisand, duets with Rita Coolidge, his demo for the Jets' 1986 hit "You Got It All" (entitled "You Got It All" (Over Him)",) an early version of "Escape (The Piña Colada Song)" called "The Law of the Jungle" which has entirely different lyrics, plus brand-new recordings of hits her wrote for the Buoys ("Timothy"), the Partridge Family ("Echo Valley 2-6809") and the Street People ("Jennifer Tomkins"), which was a studio-created group featuring Holmes on vocals. These final two discs in Cast of Characters may not be as consistently engaging as the first three, but they are certainly worth the time for anybody willing to invest in this set. And who would be willing to invest in this limited-edition, internet-only box? Well, Holmes does have legions of devoted fans, and they will surely find this worthwhile, but this could satisfy listeners with a deep appreciation for pop singer/songwriters of the '70s -- an appreciation for singer/songwriters who cherish craft over obvious eccentricities and innovation. After all, this set proves that Rupert Holmes was many, many things -- much more than what "Escape" would suggest -- but it also proves that he was never hip; not then and not now. That will surely cut down on his chances of a revival along the lines of what Brian Wilson or Harry Nilsson have experienced over the last ten years, but anybody who has heard one or two of these albums and is curious about what else Holmes did will find that this set rewards their investment many times over. [Cast of Characters is available through Hip-O Select.com].