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Opening Act

I toured all over the U.S. and Europe in the late 90s/early 00s, but never progressed beyond opening act. It would have been nice to headline – I might still be in showbiz! – but now is not the time for a post mortem. Instead, I want to brag about what I did well: entertain and sometimes captivate audiences that started out indifferent slash impatient for the main event. I know I’m right because people told me, and “voted with their wallets” by buying CDs after the show. I still get occasional “will there be new music?” and “when are you coming back to my city?” emails from people who saw me fifteen years ago. I even had some positive notices in the media:

“Hillman should be teaching classes in how to warm up an audience.”
-Seattle Post-Intelligencer

The audience was also thrilled with…opening act Bob Hillman, a performer 1/3 Bruce Springsteen, 1/3 Bob Dylan, and 1/3 Conan O’Brien.”
-Cambridge Star

“Opening act Bob Hillman was a bit like a male Suzanne Vega with a wackier sense of humor, a less-tentative Elliott Smith or perhaps a folkie Tenacious D. His set was good enough to suggest he may be one indie movie soundtrack away from bigger things.”
-Wisconsin State Journal

“Lyrics don’t get much smarter and funner than those in the songs by singer-songwriter…Bob Hillman. Hillman nearly stole the show when he opened for Suzanne Vega at the Barrymore last December, regaling the crowd with hilarious songs about communists and the pitfalls of being an opening act.”
-Capital Times

“Opening act Bob Hillman was wry and a bit loopy. It’s good to know that Suzanne Vega will not be the last quirky folkie to emerge from New York.”
-Portland Press Herald

I didn’t always kill, especially in the early years. Before I understood pacing, I used song selection and running order to severely bum out a bunch of innocent people at Fez Under Time Cafe. Another time, the impenetrable-to-some irony in early songs like List of Enemies got me permanently banned from shows with one earnest-leaning folksinger. Later, I got into trouble when I pushed the envelope on the between-song antics in Germany and Copenhagen: those audiences understood English, but I found ways to confuse them.

I had it pretty much together in time for my first big break: two shows with Dan Bern at the old Freight & Salvage in the run-up to Y2K. I was a huge fan, having been blown away by a song called Too Late To Die Young at the 6th Annual Rocky Mountain Folks Festival in 1996. By late 1999, he’d released a couple of albums on a major label, toured with Ani DiFranco at or near her peak, and developed a national following; the Berkeley shows sold out in advance. I remember feeling some pressure, and breaking a string on the first night, but still going over well with Dan’s audience. Since then, I’ve opened for him dozens of times all over the country as recently as last year.

Not every Bern gig was perfect. On a Monday night in Delaware, Dan wanted to watch the World Series, which started at around 8pm. The manager asked me to stretch my set, which was fine with me, but not so much with the audience, who assumed I was responsible for the delay. I don’t think I got the benefit of the doubt even when Dan took the stage at around 11:30pm, easily an hour after I wrapped up. I even stumbled upon some online grumbling, which may been a first, since this took place before MySpace launched in 2003.

My biggest and longest opening gig by far was with Suzanne Vega. I got to know her when she started showing up at Jack Hardy’s weekly songwriter’s meeting in New York for the first time since Luka became a hit. She’d taken a few years off to raise her child, but was writing songs again and planning a new album and tour. Suzanne dove headfirst into our little scene, joining us for post-meeting “field trips” to the Ear Inn and checking out our shows, including one of mine at the Living Room. Consequently, when I floated the possibility of opening a couple of West Coast shows for her, she knew I could handle the job. Those first two shows went well, and – despite the best efforts of an SF Examiner reviewer – turned into a year of work on the Songs in Red & Gray tour, an appearance at the Newport Folk Festival, and a ridiculous amount of fun.

Vega was booked into clubs and theaters that ranged in capacity from 500-1,500 with the occasional outlier. From the opening act perspective, theaters were preferable, because the audience was seated and engaged. The ultimate opener-friendly venue may be 500-capacity Birchmere (Alexandria, VA), where the combination of first come/first serve seating and decent food encourages early birds. Not only that, but they listen carefully and laugh at all your jokes! Stand-up venues present challenges, because there’s more of a party atmosphere. My worst night may have been at The Belly Up in Solano Beach, CA, where I simply couldn’t get anyone’s attention. Along the same lines, I always looked forward to but was slightly disappointed by the House of Blues. The exception was a 2,300-seat theater in Antwerp: it’s hard to commune with that many Belgians when you’re a solo act and don’t speak Flemish.

The Songs in Red & Gray tour gave me the idea for what became my modus operandi: (1) identify promising artist/venue, (2) monitor their calendar, and (3) propose myself as the opening act. It helped that most artists and venues had websites by this point, and that I had an agent with solid connections in the singer/songwriter world and beyond. In most cases, I made a good impression on the various stakeholders, which streamlined the process. At my peak, I was opening for all sorts of people in prominent venues on the East Coast circuit and making trips to the Midwest, California, and the Pacific Northwest.

You don’t get rich as an opening act on the singer/songwriter circuit. The going rate for a 30-minute set at a small venue like Club Passim (Cambridge), the Iron Horse Music Hall (Northampton), or the Tin Angel (Philadelphia) – three of the places absolutely everyone aspired to play – was and in fact still is $50, which won’t cover your expenses even if you stay with a friend. Sometimes, they pay you less and/or ask you to play fewer songs. Conversely, my old friend Mark Erelli once laid an extra $50 on me – out of his own pocket! – because someone had done it for him in the past. 

Not that I’m complaining about the pay: I got the exposure I wanted, made lifelong friends, and generally had the time of my life. I know for a fact that a lot of the venues are doing their part by leading new artists down a path from open mics to opening slots and double bills to headlining. The $50 model may have evolved as an informal “up or out” mechanism by which those of us who don’t break through are forced to get on with our lives or starve. I personally took the “out” door in 2003, when I was 33 and still in a position to change careers. I sometimes wonder what would have happened if I’d stuck it out, but I don’t generally regret the 90-degree turn that led to a ten-year career in marketing. As a by-product, I’m so much better at peddling my musical wares than I was in my “artistic” days!

It behooves opening acts – who aren’t the ones putting butts in seats – to remember that their mandate is to “support.” Above all, that means sticking to the schedule. I opened for Dave Alvin a few times, and was super-excited to sound him out about a Blasters show I saw at the Universal Amphitheater in the early 80s. I assumed that, since it was their biggest headlining show, he’d have fond memories and maybe a few anecdotes (I live for anecdotes from the L.A. rock scene of my formative years). The main thing he remembered from that night – I’m not kidding – was that the opener, Rank & File, had gone over their allotted time.

The trick, then, is to NOT go over, even if the club owner eats up half your time playing his own songs, which is a stunt someone pulled on me in Port Chester, NY. The problem is, it’s hard to keep track of time when you’re on stage. You can estimate the right number of songs, but I know of no analytical methodology that can forecast what happens between songs, e.g. technical problems and banter/stories. And, more fundamentally, you have to know what time you started. I usually forget to look at my watch at the beginning of my set and then spend an inordinate amount of time wondering how long I’ve been up there. There’s nothing worse than hearing “one more” from the sound guy when you’re still setting up the big finale.

The time limit includes the encore, but I can count on one hand the number of times I got an encore as an opening act. I didn’t even get an encore in the Luxembourg basketball gym when a line to purchase my CDs formed at the sound desk and extended all the way to the exit. There was obviously an appetite for more, just not right then. I did get an encore the first time I opened for Suzanne Vega at the Fillmore, but that may reflect critical mass: I had a lot of friends in San Francisco. I remember walking off to applause and raising an eyebrow at the monitor guy, who sent me back out there with a decisive nod. 

As long as they’re playing by the rules, opening acts should feel free to make an impression. The secret to success be to play great songs and play them well. But great songs aren’t always enough, given that the audience paid to see someone else. As a rule of thumb, it’s wise to solicit their attention unequivocally and expeditiously. For example, Dan Bern wrote Tiger Woods specifically to win over Ani DiFranco’s late-90s fans, who were not shrinking violets. One of the tricks I had up my sleeve was a minor ditty called Opening Act, which started as an improvisation but evolved into a set piece that always seemed to break down barriers (it may not have the same effect out of context):


There is “systematic risk” associated with the opening slot. For example, the headliner may cancel. In that situation, there’s no recourse other than to hope you can make the rescheduled date, over which you’ll have zero influence. I have my share of experience with cancellations: Suzanne Vega cancelled once because of a death in the family, and John Gorka cancelled a weekend in Texas because of a back injury. Todd Snider cancelled a sold out show at the Ram’s Head in Annapolis, MD at the last minute for mysterious reasons – according to his entertaining and illuminating 2014 book, I Never Met a Story I Didn’t Like: Mostly True Tall Tales, he was heavy into opiates in that era – and Dave Alvin cancelled three East Coast dates after 9/11 because his girlfriend didn’t want him to travel. I eventually played the Vega and Alvin dates, but had to give up on Gorka and Snider.

Speaking of Todd Snider, I opened for him a handful of times, and wanted to open for him more, because I love his songs and performance style and because he has an ardent and exuberant following. He invited my wife and I to a gathering after a gig in Santa Cruz, where I met Al Bunetta, who managed him and ran his record label. A fortuitous meeting, I thought, because my agent knew Al from the old days. During a festive evening, I gently nudged him – “hey, I’d love to open for Todd more often!” – and he seemed amenable, but didn’t remember the interaction when my agent called him the next week. I’d hung my agent out to dry! The opening act approach can be a tough row to hoe, and you should be prepared for plenty of rejection and occasional embarrassment along the way.

People I’ve Opened For

Dave Alvin
Dan Bern
Ray Bonneville
Randall Bramblett

Dennis Brennan
Pieta Brown & Bo Ramsey
Dave Carter & Tracy Grammar
Peter Case
Kris Delmhorst
Cliff Eberhardt
Stacey Earle
Melissa Ferrick
Steve Forbert
Mary Gauthier
Vance Gilbert
John Gorka
Tracy Grammar
Mark Erelli
Jack Hardy
Ray Wylie Hubbard
Janis Ian
Freedy Johnston
Lucy Kaplansky
James Keelaghan
Paul Kelly
The Kennedys
Jess Klein
Patty Larkin
Michael McDermott
The Nadas
Ellis Paul
Tom Paxton
Willy Porter
Chuck Prophet
Maggie and Suzzy Roche
Todd Snider
Eric Taylor
Louise Taylor
Suzanne Vega
The Weepies
Susan Werner

Bob Hillman Administrator


  • Mokai August 7, 2017 // 12:42 pm

    Good blog post – glad to see you writing about your experiences. I’ve know dozens of singer songwriters over the decades, and almost none who even got as far as a decent opening act. Looking at the list of who you opened for, I am wondering what set them apart, it seems I’ve known other unknowns who are as good as some of those headliners, but maybe I’m missing some element that gave them a leg up.
    It seems, for the last 20 years or so, that whatever on ramp may have once existed is gone and there is no actual path to a career for many talented folks.

  • Kate Isenberg August 7, 2017 // 1:31 pm

    I loved reading this tale. thanks, Bob.

  • Bob Hillman August 9, 2017 // 3:32 pm

    Thanks for reading, Kate!!

  • Bob Hillman August 9, 2017 // 3:53 pm

    Those acts were headlining reputable venues because people wanted to see them. That could be because they made great music, marketed themselves well, etc. In reality, it was a combination of those things with a little luck sprinkled in. I will say this: people who were good at selling themselves could make up for deficiencies in the songwriting department, and that’s still true. It’s also true that there were various onramps in those days that have been diluted today. In my experience, though, success was about as elusive then as it is now.

  • Peter Thompson August 15, 2017 // 8:19 am

    Terrific tales from the trenches, Bob! I remember when my cousin and I stumbled upon you. It was at Passim in Cambridge, not too long after WTMC was released, and you were part of a songwriter’s showcase of sorts. In all honesty, I was there to see the great Aussie singer/songwriter, Mick Thomas (of Weddings Parties Anything), as well as New England’s premier folkie, Bill Morrissey. It’s rare that the unknown guy makes an impression, but you surely did. It’s been a grand ride with your songs, and may it continue!


  • Brian L August 15, 2017 // 12:25 pm

    Bob, by my measure of “success” you are there. Having listened to a chunk of your back catalogue and being privileged to hear much of your new material as it came forward, I feel like you are incredibly gifted with a unique sound and style. I really appreciate the stories and your perspective. Commercial success is a random dice roll and you are correct that drive/ambition can help the dice be less “loaded”. It’s not the only measure by any means.

  • Ken Newman September 2, 2017 // 8:32 am

    Great piece, Bob. You’re a really fine writer. Even when the words don’t rhyme …

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