Frank Sinatra: Watertown (1970) (also, Led Zeppelin)

September 08, 2025

Frank Sinatra: Watertown (1970) (also, Led Zeppelin)

I'm by no means a Frank Sinatra fan (aside from the occasional Sunday morning kitsch-value spin, when I put my lounge music collection on shuffle-play and he might pop up). But I picked up Watertown, his 1970 commercial bomb (later subject to some critical reappraisal) maybe a decade ago when I read about it on some music blog. It was described as Sinatra's attempt at a post-Sgt. Pepper/post-Tommy concept album, at a time when every rock act was trying the same thing, a failed attempt to sound a little more contemporary; and the songs were written by Bob Gaudio (of the Four Seasons) and folk singer-songwriter Jake Holmes, the same pair who had also crafted a strange and surprisingly compelling semi-psychedelic concept album for the Four Seasons.

Watertown is a gut-wrenching break-up album, essentially a series of unsent love letters from the perspective of a man whose wife has walked out on him and their kids. It's not a rock album, musically squarely in Sinatra's orchestral jazz/pop territory, though it's not entirely out of place in a landscape that includes the Beach Boys' Pet Sounds or the Moody Blues' Days of Future Passed. A couple songs, like "I Would Be In Love" (my favorite on the album) or "She Says" (with its odd rhythm and children's chorus) could almost pass for post-psychedelic sunshine pop; "What's Now Is Now" isn't radically far afield from, say, the first strings-laden Genesis album, subbing in Sinatra's croon for Gabriel's.

But the closest counterpart in the rock world might be Lou Reed's 1973 similarly emotionally harrowing Berlin. (Interestingly, the recent CD issue of Watertown appends a contemporaneous single called "Lady Day"--sadly, not the Berlin song.) Slip on some headphones and focus on the lyrics, and those two records would make for a devasting two-fer gut-punch.

Now, I've only listened to the record a couple times since; as noted, I'm not a Frank Sinatra kinda guy. (Then again, I don't play Berlin very often, either, and I'm definitely a Lou Reed kinda guy.) But I pulled it out last week, after the record made a surprise appearance on Andrew Hickey's remarkable History of Rock Music in 500 Songs podcast.

I don't know if I've mentioned this podcast previously on these pages, but if you're not listening to 500 Songs, you need to be (certainly by virtue of the fact that you're here reading this). For several years, Hickey has been doing an (unbelievably) deep dive into music history, one song every few weeks (or sometimes a single song spread over multiple episodes) in chronological order. (So deep that he spent the first several dozen songs focused on rock's blues, country, and jazz roots; he didn't even reach the Beatles for the first time until Song #100.) While some episodes (or multi-episode arcs) remain focused on a particular song or band, the best ones are an opportunity to place music in a broader historical context, with incredibly important lessons on, say, the Vietnam War or racism in America as a backdrop for a particular song or artist.

The most recent episode, Song #180, is the first of a two-parter on "Dazed and Confused." Hickey, in his brilliantly detail-oriented and dizzyingly peripatetic fashion, carries on for two and a half fascinating hours without once mentioning Led Zeppelin by name. Instead, one of my favorite episodes to date treats us to a look at the history of the Four Seasons, pivoting into the life of Jimmy Page, and an overview of the Yardbirds' post-Eric Clapton years.

Which sort of brings us to Sinatra and Watertown. Because the Four Seasons' career artistically culminated in that surprising concept album referenced above (1969's Genuine Imitation Life Gazette). And that record's songwriters then met Frank and gave him Watertown (which Hickey takes the time to describe and praise at length). And the co-writer of those two albums, Jake Holmes, also happened to write and sing a song called "Dazed And Confused" on his 1967 solo album The Above Ground Sound. A song which Jimmy Page adapted and performed with the Yardbirds and later (as we'll find on the next episode of the podcast) recorded for the first Led Zeppelin album. (Which, like many Zeppelin songs, was credited to Page, whom Holmes later sued for due credit.)

Hickey's recent arrival at Led Zeppelin in his chronology is arguably the victim of bad timing, as last year's great Led Zeppelin documentary covers some similar ground. But there is enough divergence to make both absolutely worthwhile even for those of us who aren't particularly fans of the band (which I'm not, as noted previously in these pages and in my book).

So, anyway, bottom line: Check out Frank Sinatra's Watertown. And definitely, if you haven't yet, check out the 500 Songs podcast--start at the beginning, or work backwards from the current episode, or cherry pick the songs you're specifically interested in.

Frank Sinatra, "I Would Be In Love":