“I was totally hung over and we hadn’t seen each other in three years,” he said. “I just pulled the covers over my head and asked her to leave. This person I was totally in love with showing up after three years, it was just too much.” “Midway Park” sounds a beguiling opening note to Faithless Street. It commences with a hypnotic guitar riff (a kissing cousin to “Lonely Is as Lonely Does,” the 1984 ballad by Whiskeytown’s fellow North Carolinians the dB’s), counterpointed by Skillet’s easy-riding cymbal and Caitlin’s plucked fiddle strings. And Ryan’s vocal goes for the throat, conveying just the right edge of pleading desperation as he steps to the microphone to croon an opening line hinting at galaxies of open-ended possibility:
I’ll ride with you tonight, I’ll ride forever . . .
Line by line, the focus sharpens. That gentle cymbal builds up to a forceful backbeat, and the guitars ramp up to something resembling a snarl, goading Ryan from a croon on up to a holler. But as the sound gets more intense, Ryan’s words grow more thoughtful with wordplay contrasting the dual meanings of the verb “lie”—to tell untruths, or to repose? It means one or the other in different parts of the song, and both at the end. On the outro, Ryan’s doubled voice says “we’ll lie” and “tell a lie” simultaneously.
My first hearing of “Midway Park” on an advance-copy cassette tape left me awestruck at its simple beauty and plainspoken elegance, every piece a perfect fit. Rough as it was, it still had nary a note out of place. So I rewound that sucker and played it again, and again. Once I finally let the tape play past “Midway Park,” the rest of the album was just as impressive. Faithless Street showed remarkable maturity and sophistication, especially given the chaotic circumstances of its recording. Phil Wandscher told an amazing and very possibly exaggerated story about what it took to get the basic tracks into releasable shape.
“The guy we recorded it with was supposed to mix it, but he wasn’t getting it done,” Wandscher said in 2011. “We basically had to go steal the tapes because the dude was so strung out. He started getting really weird about things. There was a little buzz locally and maybe he felt like he could milk more out of it. So Skillet and Ryan went over there when he was nodded out, found the tapes, and heisted them. Then I had to lock myself in a studio for a solid week, not even mixing but fixing all these problems so it could sound like a record. The drums were out of phase and shit was all fucked up.”
Postproduction was more like damage control than conventional mixing and mastering, and it’s certainly true that Faithless Street will never win any technical awards for its fidelity. As is often the case with music recorded on the cheap, too much of its sound is compressed into the midrange frequencies, forcing the other instruments to battle it out with the guitars. Ryan and Phil’s guitar parts almost completely overwhelm the lower-end frequencies, especially Steve Grothmann’s bass. Faithless Street would eventually get a significant upgrade on a reissued version that came out in 1998, featuring extensive remixing by Chris Stamey and Tim Harper.
But even in its raw state without any sonic tweaking, the original low-fidelity version of Faithless Street was a stunning, exquisite debut album that caught ears far beyond the Triangle. Rough edges and all, it announced Whiskeytown as one of the best new bands in America when it was officially released in early 1996—and catapulted the group to the top of the alternative-country class.
After the introductory tone-setting bow of “Midway Park,” the second song on Faithless Street establishes Whiskeytown’s honky-tonk bona fides. The original quintet never sounded more ragged-but-right than on the first fifteen seconds of “Drank Like a River,” interlocking a stomp-along drumbeat with churning guitars and Cary’s airy fiddle hovering like a carrion bird circling overhead, drawing a bead on this song’s protagonist. “Drank Like a River” is country and punk in equal measure, drawing the second part of that equation from Ryan’s squalling lead vocal. He sounds like he’s on the business end of a crushing morning-after hangover as he describes an unfortunate soul whose life got wrecked by his darlin’, and so he tries to drink the pain away. Whiskey river take my mind, indeed.
It gets even more countrified on track 3, “Too Drunk to Dream,” thanks to a terrific pedal steel lead. Chris Riser had departed Whiskeytown’s lineup by then, leaving local session man Bob Rickers to fill in. Rickers is the unsung hero of Faithless Street, adding superb and just-right decorative flourishes throughout. But his playing is especially fine on “Too Drunk to Dream,” which he takes straight to Bakersfield, California. As for Ryan, he sings in an angelic Gram Parsons croon worlds away from the previous song’s exhausted rasp. If “Drank Like a River” could’ve been the Replacements on a honky-tonk bender, it’s easy to imagine George Jones singing “Too Drunk to Dream.”
Phil steps in as lead singer on “What May Seem Like Love,” a withering kiss-off that benefits from another stellar steel guitar part. It’s more notable for some of the poison-pen lines than the vocal performance, although Wandscher’s deadpan voice effectively conveys the angry frustration of the lyrics. Phil returns toward the end of the album as lead voice on “Top Dollar,” the penultimate track, on which he gives his Keith Richards tendencies full sway.
Caitlin’s fiddle is the star of the title track, “Faithless Street,” a renamed version of “Angels Are Messengers from God.” At that time, Faithless Street was Chamberlain Street in Raleigh, where Ryan lived in a rental house just up Hillsborough from Sadlack’s. Dressed up with some very fine pedal steel weepiness, this is better-realized than the version that appeared on Whiskeytown’s debut mini-album. The tempo is a bit more deliberate, proceeding as a waltz driven by Caitlin’s Irish-sounding fiddle.
By all rights, the following “Mining Town” is a song that should not work. The lyrics represent Ryan at his most imaginatively self-conscious, describing a played-out gold rush town straight out of some period Western along the lines of Paint Your Wagon. Ryan plays a clipped acoustic-guitar strum that lopes along at an easygoing pace, with a few unexpected accents to underscore the song’s sense of uncertainty. He sings in an exaggerated, crooning drawl—“Maybe Iiiiiiii’m comin’ for you toniiiiiight”—that sounds like it would be right in Jimmie Dale Gilmore’s strike zone. Onstage, however, Whiskeytown used to rock this one up to the point where it almost sounded like heavy metal.
“If He Can’t Have You” begins with a sparkling guitar riff that shines like a diamond. Ryan has said that this song was copped from Patty Duke Syndrome, and the guitar riff does echo a number of Patty Duke songs (“What’s Your Name?” and “Super Song,” among others). Phil dirties it up with a fiery guitar lead, while Ryan’s vocal describes the feelings of trying to reconcile an awkward breakup that leaves former lovers tripping over each other around a too-small town. In contrast to the prettiness of that opening riff, Ryan’s voice sounds angry, raw, and worn-out.
But that’s nothing compared to the next song, “Black Arrow, Bleeding Heart”—a song Ryan played that first night I saw him and introduced as “a song about what happens.” And it sounds almost delicate, even as the lyrics paint a picture of stalkerish obsession. Quiet piano and Rickers’s Greek-chorus pedal steel swoops serve as adornments—and while the lyrics open with the image of throwing rocks at a window, it sounds more like what you’d feel after throwing bricks at a mirror.
Then comes Caitlin’s big star turn on “Matrimony.” Over the years, Caitlin has taken pains to downplay the autobiographical aspects of this song. But she did write it at a time when she was very much soured on love.
“‘Matrimony’ was sort of about me at that moment,” Cary said in 2002. “I’ve always said that one is not about my parents, it’s probably about me. For a good many years, I thought [marrying] was something I’d never do. I went through a really bruising breakup in Texas, had three or four years of hating men and hating the idea of relationships. ‘Matrimony’ was written during that time. It’s funny how many people have come up to me over the years to say that ‘Matrimony�
�� got them through a breakup—‘I love that song, I just got divorced from a total bastard and that song really carried me through it.’”
Deriding married life as “misery, simply a faster way to die,” Cary sings in a straightforward and defiant voice (in waltz time), telling her story in curiously formal language that hints at no inclination to change her mind. But eventually, she did change her mind. Caitlin and Skillet were engaged by the time Whiskeytown played one of their last-ever shows, on New Year’s Eve as 1999 turned into 2000 at Cat’s Cradle. Ryan marked the occasion by serenading the happy couple with what he called “my own personal version of ‘Matrimony,’” which he sang in his best over-the-top Mick Jagger impression.
“Alanis Morissette is not ironic,” Ryan said by way of introduction that night. “This is ironic.”
Back on Faithless Street, meanwhile, Ryan returned to sing lead on “Hard Luck Story,” which is less a song than a tongue-in-cheek writing exercise. The lyrics break out almost every country cliché ever set to music in its two minutes—truckers, buckets full o’ tears, fickle hearts, bad moons risin’, drinkin’, cussin’, fightin’ in bars. Ryan claimed he jotted down the lyrics to “Hard Luck Story” on a pizza box during a spare twenty minutes of the Faithless Street sessions, and the song sounds like that in the best possible way. On a very heavy album, “Hard Luck Story” provides a much-needed dose of levity. It’s also Ryan’s most relaxed Faithless Street vocal, with Caitlin’s harmony vocal interjecting both sass and class.
After Phil’s “Top Dollar,” the last “official” song on Faithless Street is “Oklahoma,” a song originally recorded during the Angels mini-album sessions. It has the alternative-rock era’s loud-chorus/quiet-verse dynamic down pat and it’s fine, though no great shakes (especially compared with the album’s opening stretch). “Revenge,” the unlisted hidden bonus song, would have made a better hard-rocking closer. Not surprisingly, “Oklahoma” would be the one Faithless Street song to be left off the 1998 reissued version.
The reissue also added a few outtakes from the Funny Farm sessions: “Desperate Ain’t Lonely,” a new version of “Tennessee Square,” “Excuse Me While I Break My Own Heart Tonight,” and “Lo-Fi Tennessee Mountain Angel.” Parenthetically subtitled “(for Kathy Poindexter),” that last song paid tribute to the lead singer of local punk band Picasso Trigger, with lyrics that described wanting to sing country despite being in a punk-rock band. Poindexter had written a song of the same name about Dolly Parton, and Ryan decided she deserved her own version. So he wrote it. The recorded version is acoustic and quiet. Onstage, however, Whiskeytown usually played “Angel” at maximum blare, with Ryan singing at a flat-out scream.
Funny thing, years later Kathy Poindexter wound up leading a country band called Death and Taxes.
Chapter Six
Once Faithless Street went into nationwide release in early 1996, things started to happen very fast. Ryan had been right about major-label interest once word about Whiskeytown got out beyond Raleigh, and Faithless Street was a wonderful calling card. But not everyone in town was thrilled about Whiskeytown’s rising fortunes.
“To me, Ryan was always most notable because he really, really, really wanted to be a ‘rock star’ and I didn’t know very many people in the Raleigh scene who did,” Dana Kletter said in 2011. “To those of us who’d been there a while, that would be an unseemly thing to have people know about you. It was just so anti-Raleigh, not like the way people were there. His ambition marked him. One time Ryan came striding into the Rockford with that Keith Richards hairdo he was sporting for a while, a lot of rings, his whole rocker costume. He sat down and declared, ‘Well, I’ve decided to do it. I don’t care if they fuck me over, I’m gonna go for it and sign a big record deal.’ I was, ‘Great,’ and then he declared, ‘The reason you’re not doing what you want to do is you’re so fearful.’ That was the sort of thing my irritating little surfer brother says to me, and I was also about to sign another deal with Rykodisc, so as usual he had no idea what he was talking about. I told him that and he said, ‘You think I’m stupid.’ ‘No, Ryan, I know exactly how clever you are and that you’re willing to do anything, which is the problem. You’re not a bad musician, I’m just uncomfortable with the person you are and I’m not like you.’ He said, ‘Whatever.’”
Clashing worldviews and jealousies aside, Whiskeytown’s potential move to a major label raised another issue in that the band was already under contract to a label. But Mood Food was small, while Whiskeytown’s potential was large. It was obvious that a big label was going to buy out Mood Food and take Whiskeytown up to the big leagues. Signs pointed toward that happening at South By Southwest, the annual industry convention in Austin, Texas.
But South By Southwest wouldn’t happen until March, and Whiskeytown weren’t playing live much, because Caitlin Cary and Steve Grothmann were busy with school that semester. Give Ryan Adams a spare couple of months and he’s liable to start a new band. And that is precisely what he did in early 1996, forming a short-lived ensemble called Freight Whaler. The ever-loyal Skillet Gilmore was on drums, with two members of the band Ithica Gin—guitarist Sloane Doggett and bassist Chris Laney—plus pedal steel guitarist Nicholas Petti, who had replaced Chris Riser in Whiskeytown by then. Freight Whaler were more of a standard roots-rock outfit than Whiskeytown, and they mostly served to muddy the waters for a brief time as to which band Ryan was really in.
My most vivid memory of the group was seeing a show where Ryan cryptically announced after each song, “Freight Whaler pushes the rock envelope!” It was good, though far from envelope-pushing. But as with all of Ryan’s endeavors, Freight Whaler began with much promise. Laney still remembers the initial band meeting to talk things out, when Ryan could not sit still.
“He was literally standing on top of the couch while we were getting to know one another,” Laney said in 2011. “Sloane compared Ryan to Peter Pan afterward. It was almost more literal than the classic ‘Peter Pan Syndrome’—the way he’d float around the room literally climbing on things. He was just so excited, and his excitement for music was monstrous. When he’d talk about it, he just couldn’t contain himself. He’d be coming out of his skin.”
Even though there wasn’t a liquor reference in the name, Freight Whaler were just as alcohol-intensive an experience as Whiskeytown. Wes Lachot, who produced a Freight Whaler recording session, recalled that Ryan’s in-the-studio methodology was to do a few takes and then “get drunk and listen to them to see if they sounded any good.” Things played out similarly onstage, such as a disastrous February 1996 show in Chapel Hill. Freight Whaler were opening for the Scud Mountain Boys, a Massachusetts band that was one of Laney’s all-time favorites.
“Ryan was going through some stuff,” Laney said. “A&M Records was interested in him and didn’t seem to know if Whiskeytown or Freight Whaler was his band. Ryan was in a weird state with his girlfriend, and A&M had sent this girl to chase him around, too. All kinds of stuff was going on, extracurricular activities, and Ryan got inebriated. He’d sometimes do this high-pitched Prince vocal thing, and he did that. And there we were, playing for this enormous band to us, and he fell back into the drums. Knocked them over. ‘Oh my God, are you serious?!’ But he jumped right back up and we all helped get the drums back in place.”
Freight Whaler’s recording session was a one-day affair in the dead of winter. Skillet made it through even though he was nursing a broken collarbone, sustained while falling off a skateboard onto ice (in an act of pity, Lachot gave the chronically broke Gilmore fifty dollars afterward so he could go to a doctor). While those recordings have never been released, the Freight Whaler song “Bar Lights” would later be the final track on Whiskeytown’s last album—but that was a few years down the line. Soon enough, Freight Whaler were mothballed, and Ryan went back to concentrating on Whiskeytown.
With record labels starting to sniff around, Whiskeytown needed a manager. That’s when Jenni Sperandeo entered the picture, by w
ay of the Replacements—the lovably scruffy band from Minneapolis that changed many lives during the 1980s, including Sperandeo’s. She was studying prelaw at Michigan State University when she first heard the Replacements, who inspired her to start working at the college radio station.
After graduating in 1992, Sperandeo started an independent radio promotion company called Jackknife with a focus on alternative-country bands, which put her in touch with bands, radio stations, and record labels. She was also a regular on the No Depression Folder. And when No Depression started up in 1995, Sperandeo was the magazine’s first advertising director, because she knew pretty much everybody in the alternative-country world. Then Whiskeytown entered her field of vision and pushed all the same buttons the Replacements had. Ryan asked her to manage the band, and, with some hesitancy, Sperandeo gave up selling ads for No Depression and agreed to take on the band. Overseeing Whiskeytown’s affairs was to be a wild experience, but Sperandeo and her managing partner Chris Roldan had an appropriately jaded perspective on it.
“Ryan was definitely dialed into The Myth at all times,” Sperandeo said in 2011. “It sprung from his own head, fully formed. Even when Ryan was Mr. Drinker and doing a lot of drugs, it didn’t worry me as much as it should have, because I was young and stupid and really into the band. But at the end of the day, Chris and I would look at each other and say, ‘Anybody who spends his own money to have his teeth capped is not gonna kill themselves.’”
South By Southwest 1996 would be alternative country’s big moment of promise, and Whiskeytown were just one of several insurgent-country acts who came to town as the object of major buzz. Another was from right up the road in Dallas, the Old 97’s. Whiskeytown and Old 97’s were booked onto the same South By Southwest showcase bill at a downtown Austin club called the Split Rail. Numerous major-label representatives were there to see what all the fuss was about.
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