What Event Planners Can Learn About Booking Entertainment from Woodstock 50

The much ballyhooed 50th anniversary of the Woodstock music festival ended up a gigantic bust. Why? It suffered from some of the same challenges you face in selecting and booking entertainment for your events and conferences. Here’s what your next event can learn from Woodstock 50.

A Well-Known Challenge

1969 was the Summer of Love. The original Woodstock Music & Art Fair attracted over 400,000 people and became a worldwide milestone event in music history. The organizers saw a fantastic opportunity to recreate the same vibe and announced that Woodstock 50 would be held in August 2019. Slam dunk, right?

Just two weeks before it was scheduled to begin, it was canceled. The reasons were many, but right at the top were three main challenges:

  1. Location
  2. The right entertainment
  3. Entertainment agreements, contracts and riders

I bet that list looks familiar! It’s the same one you and every organizer and producer faces when selecting and booking entertainment for association conferences and corporate events.

Location, location, location

The dream was to go back to Watkins Glen, the site of the original festival. But fifty years had gone by and the location was wrong and too small. After finding and losing four different locations, organizers had to admit their vision wouldn’t fit.

Hard fact: Whether it’s a giant festival or special entertainment for an event, the same rules apply.

  • The location has to fit the size of the entertainment.
  • The entertainment has to fit the size of the location.
  • It has to have the right access, security, power and approvals.

Be Logistics Savvy

If you have a small ballroom and 100 people, you can’t book a 15-piece band with a 60-foot stage and expect it to fit. Conversely, putting a three-piece combo in the middle of a 60-foot stage in a giant ballroom with 1500 people is like a marble in a barrel. That means the location has to be your number one consideration. The technical stats and logistics must come before the creative. So always decide:

  • How many people will attend?
  • How much space is available
  • Will people be sitting or moving around?
  • How long is the event?

At Woodstock 50, they were considering helicopters and a convoy of semitrucks. The state and local officials said, “No way.” Before you consider staging your entertainment any space other than the convention areas … don’t book talent until you have handled all the details. Here’s why.

Great Idea, Wrong Place

Quick story: The client was excited to have booked a major act for their dealer event. They found the perfect place on the sweeping lawn next to the hotel for the stage, lights and sound. Everything looked great for a dream evening event until the hotel checked with the other corporate group that was also using the hotel. This group wasn’t excited to have a rock concert outside their hotel rooms until close to midnight. The client canceled the group, paid a penalty and had to find a different location and entertainment. That’s what Woodstock 50 had to do to the tune of millions of dollars.

The Right Entertainment

Great entertainment is the whole idea. The key is to find performers that the audience would be excited to see. It’s not to find performers that the company president or CEO likes. The challenge is to try to please as many people as possible.

Woodstock 50 put together such an eclectic array of acts that most people found it confusing. They tossed around names from Beyoncé to Arlo Guthrie. Was it new and fusion or old and nostalgic? What experience would be just as relevant to 20-year-olds as it would be to 65-year-olds? No offense intended, but did they really expect 150,000 people to come to see Arlo? In the end, the talent mix wasn’t right.

If you don’t want to make the same mistakes, then do some planning. Make sure you know:

  1. Your budget range
  2. Who is touring near your event date
  3. What type of acts are best for your audience

Don’t guess about Number 3. The most effective way is to simply ask the audience in advance. Send out an informal survey regarding the type of entertainment that you might have at your event. Don’t list specific acts or performers, but ask about what people would be excited to see. You might be surprised by what you learn.

Entertainment Agreements, Contracts and Riders

Just weeks before Woodstock 50, most of the acts dropped out. The official story was that the performers had “lost faith in the festival.” The truth is most of the entertainment contracts and riders weren’t finalized. Remember, half of show business … is business. Negotiating agreements and contracts doesn’t have to be adversarial and difficult. You just have to understand how the game is played. You want the best talent at an affordable rate. The talent manager wants to get the highest reasonable rate for the talent and to ensure that they will be comfortable and successful.

Everyone Wants a Great Show

Everyone wants a great show and an exceptional experience. The trick is to be realistic. Remember, talent managers do this every day. Their job is to fill the act’s or performer’s schedule so they work consistently. That means managers know the contracts inside out and are experts at negotiating for their clients. Unless you book a lot of entertainment each year, you probably can’t match their level of experience. Since we are giving you three things to remember, here are some more.

  1. Use an attorney
  2. Use a very experienced agency.
  3. Book as early as possible.

The closer you are to your date, the less negotiation power you have. The calendar is not your friend.

DYI Entertainment Booking

I guess it’s a case of “Can you do it?” versus “Should you do it?” If you have the time and the experience to search schedules, check availability, review references, view demo tapes and negotiate contracts, then you will possibly save some money. If you don’t, then work smart with an experienced agency like Aquarian. I admit I’m biased, but they are excellent.

After you give an agency the details of the time, date, location size and the type of entertainment you want, they do all the research. They’ll get back to you with a shortlist of performers, availability, quotes and demos. When it gets to the final contracts and riders, they have the same experience level as the talent managers. The agency works for you with advice and guidance on selection, contracts and logistics.

The Experience of Legends

Fifty years later people still remember where they were during Woodstock. They brag about being there, even if they weren’t. How would you like to have entertainment and an event that your audience will talk about for years? Again, the key is to focus on the details that create that amazing experience.

  1. Location
  2. The right entertainment
  3. Entertainment agreements, contracts and riders.

Aquarian, a Shepard company, is ready to work with you. We know how to make it happen. We want to help you make the entertainment at your next event or conference the experience of legends.