When I first started this job back in April 2011, I was subjected to an EW tradition: I was sent a list of questions whose answers made up an office-wide introduction to my cultural obsessions. When it came time to express an all-time favorite from the music world, I settled on the one name I always shout out whenever anybody asks me what songwriter I defend above all others: Greg Dulli.

Dulli has made excellent work I have absolutely adored in several different guises, including the Twilight Singers, the Gutter Twins, and the Backbeat Band. But he got started with the Afghan Whigs, a mercurial indie rock/R&B hybrid from Cincinnati who first appeared on the scene with the haunting Big Top Halloween in 1988 and wrapped up their original run with 1998’s 1965. (They recently reconstituted for an ongoing series of shows and the brand new album Do To The Beast, which came out earlier this year.) Their masterpiece is, undoubtedly, their 1993 major-label debut Gentlemen, which is getting the deluxe reissue treatment today in the form of Gentlemen at 21. The new version contains a remastered version of the original record, plus a second disc of demos, B-sides, and live tracks that further flesh out the strange and wonderful universe the band helped create more than two decades ago.

Gentlemen has been a cornerstone album for the better part of its existence (and, subsequently, mine), so in honor of this definitive work now being able to legally order a boilermaker, here are 21 thoughts about Gentlemen.

1. To understand the context of Gentlemen, you first have to look at the context surrounding the release of the Whigs’ previous album Congregation. Congregation was released by Sub Pop, who had also put out the band’s previous album Up In It in 1990 (and who also put out Do to The Beast). By the time Congregation was released at the end of January 1992, another Sub Pop-related album had gone to the top of the Billboard album chart: Nirvana’s Nevermind. Nirvana’s success was a double-edged sword for the Afghan Whigs, as while its success almost certainly helped facilitate Congregation‘s release, radio didn’t embrace the Whigs’ sound because it strayed so far from what was quickly becoming known as grunge.

2. The Afghan Whigs didn’t let any of those issues get in the way of their plan, which was to tour the hell out of Congregation and to work on the songs that ended up becoming Gentlemen while they were at it. As Dulli noted last week, Gentlemen was crafted almost entirely on the road, and the songs were heavily road-tested by the time they got to the studio to record.

3. As the demos included on Gentlemen at 21 show, they really did have the bulk of the songs figured out by the time any tape rolled. For example, while “Debonair” has a relatively intricate arrangement and some fascinatingly weird rhythmic stuff going on underneath the hook, all of that is almost entirely there in the demo. The final version is louder and cleaner, but “Debonair” was fully-formed by the time the demos were recorded.

4. Those demos were recorded in Cincinnati, in a studio that sat over a pottery shop. When it came time to record the album in full, the group decamped to Memphis on the suggestion of Dulli associate and former Big Star drummer Jody Stephens. Not only did Stephens find the group a studio and get them set up with places to live, but he also contributed backing vocals on “Now You Know.”

5. Outside of Stephens and Dulli, the other voice heard on Gentlemen is that of Marcy Mays, who takes the lead on the lovely, downtrodden “My Curse.” Mays fronted a spectacular trio from Ohio called Scrawl, who released a series of stunningly raw albums including the Steve Albini-helmed Velvet Hammer and the moody Travel On, Rider.

6. Let’s talk about “Debonair,” which is by far my favorite song on the album. When I spoke to Dulli last week about the song, he noted that he was attempting to marry the Jackson Five’s “I Want You Back” with the theme song from Twin Peaks. He thinks he nailed it, and I’m inclined to agree with him: It has the buoyant funk of the Jacksons’ signature hit mixed with the escalating discomfort of Angelo Badalamenti’s iconic score.

7. The video for “Debonair” is pretty typical of early ’90s indie, as it’s built around the inherent weirdness of the suburbs and features both a tracking shot that makes it looks like a room is moving (perfected on Jamiroquai’s “Virtual Insanity”) and Dulli’s jazz beard.

8. That video also has a lot of shots of kids, which is thematically consistent with the famous cover of Gentlemen. It’s a take-off on a famous series by Nan Goldin called “Nan and Brian in Bed.” It was somewhat controversial at the time—Linda Ronstadt, who was also signed to the Whigs’ label Elektra, was reportedly upset by it. Of course, it’s amazing how time softens these things—last year, the cover was parodied by Lil Bub and Grumpy Cat.

9. Most of the songs on Gentlemen have what Dulli describes as a “self-flagellating” quality, and that’s because they were primarily written in response to a tumultuous breakup. Dulli was also deep into drugs at the time—according to Bob Gendron’s excellent 33 1/3 volume on Gentlemen, the bulk of the album’s vocals were recorded during a single coke binge.

10. I first got into the Afghan Whigs when I saw the shaggy, sexy video for “Conjure Me” on MTV’s 120 Minutes. I dug it, though in the days before Amazon (or even CDNow), I had no luck tracking down copies of Congregation at my local record stores. Flash forward to the beginning of 1994, when my entry into Columbia House allowed me to snag both Congregation and Gentlemen (among a dozen other records) for only a penny (and then a whole heap of debt later if you forgot to cancel).

11. My favorite song on Gentlemen has always been “Debonair” (I remember scrawling the lyric, “I fell apart, that’s what I always do” on a notebook, because I was super emo even though I didn’t know it yet), but on first listen, “Debonair” was tied with “What Jail Is Like,” which still sounds incredibly savage. Twenty-one years later, Dulli snarling, “If you want to scare me, you’ll cling to me no matter what I do” is still hair-raisingly angry and sad.

12. Most of the time when I reveal my affinity for the Afghan Whigs, I am met with one of three reactions: People who have never heard of the band, people who love the band, and people who only know the band because Gentlemen‘s “Fountain and Fairfax” was on the My So-Called Life soundtrack album. Considering what a ratings disaster that show was, it’s astonishing how many people owned that soundtrack.

13. That’s not a knock on the My So-Called Life soundtrack, by the way: It’s got a great Buffalo Tom song on it (though not the one made famous on that show’s best episode), a pretty sweet Juliana Hatfield track, and a tune by alt-nation never-weres Madder Rose, who were a great gloomy girl band who I saw open for Bush in 1995. These are all facts.

13. Gentlemen had a total of three official singles: “Debonair,” the title track, and “What Jail Is Like.” The latter didn’t get a video, but “Gentlemen” did, and it’s great: It finds Dulli in full peeping-vampire mode, minus the jazz beard but plus a really cool leather jacket that I coveted back in ’93.

14. Usually the bonus stuff on reissues is not particularly interesting (unless, of course, we’re talking about Oasis), but the extra tracks on Gentlemen at 21 are fascinating for fans of the band. There’s the demo of “My Curse,” which features Dulli on lead vocals instead of Mays, and while he does it justice, it does feel like a slightly different song when the genders are switched.

15. There are also a series of covers, which the Afghan Whigs have always kept as part of their arsenal. My favorite is a banjo-assisted version of “Mr. Superlove,” a track by indie one-hit wonders and fellow Cincinnatians Ass Ponys. Like much of the Whigs’ takes on other people’s songs, it’s haunting.

16. The Afghan Whigs have performed on stage with Usher twice, both times backing him on the song “Climax.” Even though he was only 15 years old at the time, Usher also had a big milestone in 1993: A few months before the release of Gentlemen, Usher released his debut single “Call Me a Mack” (which was on the soundtrack to the Tupac/Janet Jackson vehicle Poetic Justice).

17. The bonus material on Gentlemen at 21 also includes a cover of a song called “Ready,” which is by Marcy Mays’ band Scrawl. The recording comes from a session in Cincinnati, with Mays and Dulli blending phenomenally on harmonies.

18. It’s unclear how many copies Gentlemen sold, but it has no RIAA certifications and it never appeared on the Billboard 200. The band didn’t appear on the album chart until 1996’s Black Love, and they peaked this year when Do To The Beast made it to number 32.

19. Speaking of Black Love, that album rules too. It began as a series of ideas for a soundtrack to a film Dulli was going to produce, but it ended up being just a series of kickass songs. It’s probably the least funky of the band’s albums, but it’s got a sinister after-hours vibe that would inform a lot of Dulli’s work as the Twilight Singers.

20. Around the time of Gentlemen‘s release, Dulli was working on the soundtrack to the movie Backbeat, a somewhat forgotten 1994 movie about the Beatles that is set in their early Hamburg days that starred Stephen Dorff as Stu Sutcliffe. The movie is not bad, but the soundtrack is worth tracking down, as it features recordings of songs the Beatles were covering during their pre-fame club days. The band on the soundtrack, led by Dulli on vocals, also included Soul Asylum’s Dave Pirner, Thurston Moore of Sonic Youth, Dave Grohl, R.E.M.’s Mike Mills, and Henry Rollins. Here’s the band absolutely shredding at the 1994 MTV Movie Awards.

21. Gentlemen at 21 is available now both in digital and CD form, and there’ll be a special limited vinyl edition showing up on Record Store Day, which is Nov. 28. Get excited.

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