Singer-songwriter records new EP with half of the Fray — seriously

There's an element of humor inherent to Sam Craighead's songwriting that has, on occasion, bled into his approach to music promotion.

For his 2017 record, Tuesday Night Music Club, Craighead invented an inept fake manager, Jason Sandalwood, aka Management by Jason, whom he “employed” to communicate information about the album — complete with active Gmail and Twitter accounts. In one email originating “from the desk of Jason” and passed on to Alive by Craighead, Sandalwood struggled with simple tasks (“hey i can't figure out how to do the attachment can you help”), quickly earning the musician's ire. “My manager is an idiot (see below),” Craighead wrote above the forwarded message. In the same email, Craighead promised a new music video starring Kevin Federline (the video never materialized).

So when Craighead emailed in late February, writing that he had “recorded an EP with half of the Fray and it sounds like what you would expect, but a little less than the Counting Crows like that,” the instinct was to dismiss this news as yet another elaborate in-joke — an urge that dissipated when Fray guitarist David Welsh joined Craighead for a Downtown interview in late March.

“I just cold-called [Craighead]. Well, cold-emailed him. Whatever that term is in the 20th century,” said Welsh, who relocated to Columbus with his wife two years ago to be closer to family. “When we moved, right when we realized [the Fray] was going to be touring far less than I thought, and right when I realized that I would have more time on my hands than I thought, I started digging around to see who was here and who was making music, and it didn't take long to see a Stereogum piece about Sam. … The first 20 seconds I heard of that record, it was like, ‘That's cool. He's got his own thing going. It doesn't sound like he's trying to be a 25-year-old pop star.”

“And then you found out I am,” interjected Craighead, who will celebrate the release of a new five-song EP recorded with producer Welsh, Self Portrait w/Fries (Head2Wall Records), with a concert at the Oracle on Saturday, March 30. (Fray drummer Ben Wysocki also appears on the recording; at the Oracle Craighead will be supported by musicians Summer Sherman on bass guitar and backing vocals and David Fowler on drums.)

The increased sincerity around the promotion of Self Portrait is reflective of the album itself, which finds Craighead dialing back some of his sardonic wit, particularly on the stately ballad “Casual Laidback Sunday” and a stripped-bare cover of Rickie Lee Jones' haunting “Skeletons.” “I think I've reached a point where I need to be a little bit more clear that I'm not just fucking with people all the time,” he said.

This realization struck Craighead when he performed at a Los Angeles variety show for a friend leaving the California comedy scene, during which Craighead found himself singing and playing piano in between sets from high-profile comedians like Scott Thompson of “The Kids in the Hall.”

“I had never performed in that context before, where it's only people doing comedy, and while I enjoy getting a laugh onstage, I'm not used to people laughing at everything because they've sort of been conditioned to laugh,” Craighead said. “There was a song about my friend Gary, the rapper Mission Man, getting fired from Papa John's, and I'm not trying to make fun of him or be like, ‘Yeah, this guy's an idiot,' and I was singing that and people were cracking up. … It's the same thing with you getting the email about [the Fray] and wondering, ‘Is he joking?' … I can be sort of serious.”

Witness the EP-opening “SF Blues,” on which Craighead wanders the aisles of a San Francisco Target, debates the relative merits of the burgers dished up by Five Guys and Mel's and exercises in the hotel gym, all in an effort to distract from the sick dog he left at home. “Try to get my mind off how he's dying faster than before,” Craighead sings in a line that has the effect of coloring everything that arrived before it.

Indeed, even darkly comic songs like “Summer Buns,” which contains a couplet about a funeral pyre burning in a McDonald's ball pit, and “Kevin's World,” are written partially in service of larger, more serious ideas: consumerism and toxic masculinity, respectively.

“I think I was starting to see all the different forms that toxic, disgusting masculinity can take on, not just in the culture, but in myself,” said Craighead, who penned “Kevin's World” after revisiting relics of 1990s pop culture where the self-professed “nice guys” were often as misogynistic, self-centered and problematic as the villainous jocks. “How do I identify the things I've done and atone for that, or move past it in some way? I don't think it would be fair for me to be critical of it without also acknowledging, ‘Yeah, I'm part of the problem. And hopefully I can make myself not anymore.'”

Musically, Craighead and Welsh embarked on a similar search, often auditioning tracks in multiple skins before settling on a final take. “Casual Laidback Sunday,” according to Craighead, existed as an INXS version, a Wallflowers version, a French house version and a Lou Reed/Berlin version, among a handful of others, before it landed in its finished form. “I think a lot of the production came down to … asking, ‘Is this enhancing what the song is trying to say?'” Welsh said.

From the onset, Craighead allowed Welsh free rein to build on the music — the two said the synth-heavy tone of the EP's production was partially shaped by bad, 1980s Paul McCartney — a hands-off approach Craighead wanted to attempt in an effort to shake new ideas loose after two decades spent writing and recording.

“And, honestly, the way I'm writing my own stuff now is totally different as a result of us working together,” Craighead said. “Before it was like, ‘How many little different melodies can I layer in from every instrument I know how to play?' … Now it's really opened up and it's just about getting that vibe right and knowing when to not play something or not do something. Somehow it took me 20 years of songwriting to know when to stop. I still don't totally get it, but I'm getting there.”