Our top 10 Whiskeytown songs list looks at the catalog of an American band famed for its short yet remarkable stint as a contributor to the ‘90s alt-country scene. The band was formed in 1994 by vocalist Ryan Adams in conjunction with guitarist Phil Wandscher, drummer Eric Gilmore, bassist Steve Grothmann, and violinist Caitlin Cary. During its short stint, the band’s lineup kept evolving—Ryan Adams and Caitlin Cary were the only constant members of the band in all of its incarnations.
Whiskeytown’s alt-country explorations were heavily inspired by the musicianship of Gram Parsons, an iconic country rock artist known for his membership with The Byrds, The Flying Burrito Brothers, and The International Submarine Band. Whiskeytown proceeded to issue three studio albums and a few EPs before halting its musical pursuits in 2000.
The band’s hiatus came after endless disputes between the band members. Often, this would lead to lineup changes. Nevertheless, Whiskeytown managed to make a mark in the alt-county scene often compared with the bands Blue Mountain, Drive-By Truckers, and Blood Oranges for incorporating more rock influences to their alt-rock soundscapes.
A Quick Review of Whiskeytown’s Albums
In 1995, Whiskeytown issued their debut studio album Faithless Street. The album was issued through Mood Food Recordings, a label (once) home to Knobs, Valve, Licorice Roots, The Milagro Saints, Gordon Free, and Satellite Inn. Faithless Street is home to popular musical gems by Whiskeytown such as “Drank Like a River,” “Midway Park,” “Faithless Street,” and “Hard Luck Story.”
The album was later reissued in 1998 through Outpost Recordings under the production of Chris Stamey, a former member of the power-pop group The dB’s. As a producer, Chris Stamey has also worked with multiple artists including Hazeldine, Le Tigre, The Butchies, Polyn, and Peter Blegvad.
Whiskeytown returned in 1997 with their second studio album Strangers Almanac. The album was issued through Geffen and Outpost Records under the production of Jim Scott. Other artists who have worked with multiple Grammy Award-nominated record producer Jim Scott include Styx, Joe Satriani, The Flatlanders, and Tedeschi Trucks Band.
Stranger Almanac saw the band serve its fans with a taste of its alternative country soundscapes. The album was greatly a success thanks to the musicianship of Whiskeytown members, especially the amazing songwriting skills of Ryan Adams. “16 Days,” “Excuse Me While I Break My Own Heart Tonight,” “Dancing with the Women at the Bar,” “Everything I Do,” and “Inn Town” are some of the best Whiskeytown songs from the album.
Pneumonia, issued in 2001, marked the band’s third and final full-length studio album. The album was issued through Lost Highway Records, a label (once) home to Paul Westerberg, Whiskeytown’s vocalist Ryan Adams, Fionn Regan, Morrissey, Golden Smog, Willie Nelson, and Lucinda Williams. Pneumonia came at a time Whiskeytown members had already decided to call it quits.
The album production work was handled by record producer Ethan Johns. Other artists who have worked with Ethan Johns include The Vaccines, Kaiser Chiefs, Crowded House, Ray LaMontagne, and Paul McCartney. Pneumonia was warmly received thanks to the alluring musical quality of songs like “Jacksonville Skyline,” “Sit & Listen to the Rain,” “Easy Hearts,” “Crazy About You,” and “The Ballad of Carol Lynn.”
Despite having been active for a short stint, Whiskeytown remains a significant band in the music scene. The band is notable for its continued efforts to shape the alternative country scene. Whiskeytown’s three studio albums are among the classic releases of the ‘90s alternative country scene.
We cannot forget to mention Whiskeytown’s ability to blend raw emotions in their songs. This resulted in crafting a unique musical identity earning the band a dedicated fanbase. The band would eventually prove to be a perfect launchpad for Ryan Adams’ solo career. Here we take an introspective look at the top 10 Whiskeytown songs of all time.
#10 – Factory Girl
Ushering us to the top 10 Whiskeytown songs list is the dazzling hit “Factory Girl.” The song is one of the most revered picks from Whiskeytown’s 1997 extended play In Your Wildest Dreams. “Factory” was composed by Ryan Adams in conjunction with the band’s then-guitarist Phil Wandscher.
Ryan and Wandscher showcase their amazing craftsmanship by churning out alt-country tracks with evocative storytelling. “Factory Girl” tells the story of a young lady working in a factory and the challenges she encounters in her daily life. Ryan’s vocal delivery in this track captures the vulnerability of the lady and a sense of empathy and understanding of her experiences.
#9- Hard Luck Story
Ryan Adams knows what to do when love is unrequited—that’s a breakup with someone as depicted in the song “Hard Luck Story.” A bucket full of tears as depicted in the song showcases the emotional torture that the singer had to go through while still in the relationship. However, no more tears for the singer since he is now gone.
Of course, goodbyes aren’t so good—the singer mentions that leaving wasn’t the best of the options but he had to do it either way. Adding to the reasons why Ryan’s return to the hands of the lady is the fact that he is certain about her already actualized move—that’s moving on to her next “victim.” “Hard Luck Story” is a surefire prototypical heartbreak song.
The backing vocals of violinist Caitlin Cary add some allure to the vocal delivery of this song. “Hard Luck Story” is by far one of the most alluring tracks off Whiskeytown’s debut studio album Faithless Street. Amazing is the fact that the song “Hard Luck Story” was penned in a very short time. The band was already in the studio—the song was penned and recorded in a matter of minutes after it was composed. Michael Cerveris & Loose Cattle delivered a live cover of the song “Hard Luck Story” in 2013.
#8- Everything I Do
Coming in at the eighth spot on our top 10 Whiskeytown songs list is the alluring track “Everything I Do.” The song is one of the prime cuts off the band’s sophomore studio album Strangers Almanac. “Everything I Do” has lyrics that showcase the deep yearning and sadness that is packaged with missing a loved one.
The guitar work in this pick is quite prodigious—you’ve got to love how the guitars perfectly blend in with Ryan’s vocals. “Everything I Do” is served in a slow tempo with some melody that seamlessly communicates the song’s mood. Without a doubt, the song is absolutely a masterpiece!
#7- Sit & Listen to the Rain
Whiskeytown’s album Pneumonia was quite a momentous record—in fact, most of the band’s fans quote it to be quite similar to some of Ryan Adams‘s solo work. No song proves this better than the classic cut “Sit & Listen to the Rain.” “St & Listen to the Rain” was solely penned by Ryan with its lyrics expressing the singer’s numbness and uncertainty about his future.
Emptiness and feeling blue are some of the themes boldly enunciated in this song. The song’s title is a metaphor for one’s need to take an introspective look at their lives. Of course, we missed out on listing some massively loved hits from the album Pneumonia. However, the themes explored in “Sit & Listen to the Rain” makes it a must-have track on this list.
#6- Dancing with the Women at the Bar
Ranking sixth on our top 10 Whiskeytown songs list is the excellent track “Dancing with the Women at the Bar.” The song is yet another impressive pick off the band’s sophomore studio album Strangers Almanac. “Dancing with the Women at the Bar” serves as a reminder of how good Ryan was a great lyricist even before pursuing his solo career.
Together with the song “Inn Town,” “Dancing with the Women at the Bar” is pegged around Ryan’s tales of wasted nights. In the song, Ryan Adams recalls his love for the nightlife scene. The singer goes on to mention that this is not a far-fetched behavior—after all, his father had quite a penchant for the same as stated in the song.
However, like “any other man,” Ryan is quite concerned that his soulmate might be somewhere watching him do his “nasty” things. “Dancing with the Women at the Bar” is just a stamp of validation of Ryan’s hedonistic youth life. The song was covered by Gutter Swan and Kyle Richards and The TM Collective.
#5- Houses on the Hill
Whiskeytown’s 1997 extended play Theme for a Trucker was quite a momentous limited-edition release. Proof of this claim is the fifth pick on our top 10 Whiskeytown songs list “Houses on the Hill.” Thanks to the impressive quality of this song that it found its way to the band’s sophomore studio album Strangers Almanac.
“Houses on the Hill” is a continuation of Ryan Adams’ evocative storytelling. Notably, Ryan composed this track with his fellow bandmates Caitlin Cary. His vocal delivery in this song also channels quite some emotional depth which perfectly blends in with the song’s lyrics.
#4- Easy Hearts
“Easy Hearts” is yet another song by Whiskeytown whose glory lives on date. The song is featured on the band’s third and last full-length studio album Pneumonia. “Easy Hearts” is among the songs that perfectly capture the band’s ability to craft earnest and emotive alternative country songs. The heartfelt lyrical content of this track adds a touch of melancholy to its overall delivery.
“Easy Hearts” was composed by Ryan Adams in conjunction with Caitlin Cary. The duo also delivers superb vocal harmonies in this impressive pick giving the song a rich alt-country texture. “Easy Hearts” disappoints not when it comes to the instrumentation—the twangy guitars add quite some appeal to this track making it a worthwhile song on our list.
#3- Excuse Me While I Break My Own Heart
Ranking third on our top 10 Whiskeytown songs list is the terrific hit “Excuse Me When I Break My Own Heart.” The song is one of the brightest picks from the band’s sophomore studio album Strangers Almanac. “Excuse Me When I Break My Own Heart” is delivered in a cranking tempo that complements the emotions ranted by the singers. The song was penned by vocalist Ryan with the lyrics showcasing a deep plunge into his emotions.
Ryan sings about how drinking day and night is his hope to make the situation better, albeit unsuccessfully. “Excuse Me When I Break My Own Heart” features some vocal contributions from the punk rock/alt-country/roots root singer-songwriter Alejandro Escovedo. Alejandro has also worked with other artists including Ry Cooder, Bobby Bare, True Believers, and Mike Flanigin among others.
#2- Jacksonville Skyline
Listening to songs like “Jacksonville Skyline” proves that the future still had something to offer for the band Whiskeytown. However, it’s Ryan Adams who managed to reap the glory Whiskeytown had cultivated for some while through his solo career. “Jacksonville Skyline” is the most sought-after song from the band’s third and final studio album Pneumonia.
The song finds Ryan recalling a small-town tale that evokes memories from his childhood. “Jacksonville Skyline” is among the songs by Whiskeytown that continued to resonate with Ryan Adams. We witnessed the singer perform the solo version of this track on his 2011 acoustic tour.
#1- 16 Days
Number one on our top 10 Whiskeytown songs list is the alluring hit “16 Days.” The song is the band’s signature track and the most sought-after song from the studio album Strangers Almanac. “16 Days” finds Ryan regretting his actions and wishing he stayed with his lover instead of being away from her—the guilt seems to be taking a toll on him.
The song is yet another pick that allows us to experience the impressive vocal harmonies of Ryan Adams and Caitlin Cary. Ryan admitted that he might have sabotaged the song’s prospects to become a greater hit. The song was getting some airplay until the day Ryan dared an influential programmer to take “16 Days” off air—his lame wish was granted leaving the song to vanish from the airplay immediately. “16 Days” has been covered by The Clarks and Wade Bowen.
Top 10 Whiskeytown Songs article published on Classic RockHistory.com© 2023
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