Nineteen-year-old Edith Hilliard was standing in line in downtown Madison on December 10, 1967, waiting patiently to see one of the greatest singers and entertainers in the world, Mr. Otis Redding. In her mind, she knew that on this night there was more than a slim chance that she would meet the handsome superstar she loved so much. In fact, in her mind, it wasn’t so much of an “if” question. It was “when.”

“Oh, I planned on meeting him!” Hilliard laughs. “My friends and I thought that there would be an opportunity because there were so few African Americans there. So, we figured there’s just a little group of us and he’s gonna recognize that and he will definitely want to say something to our little group of people. So, yes, absolutely. That was the thought. We just knew that that was going to happen.”

Redding was touring the nation less than six months after his electric performance at the Monterrey Pop Festival in the summer of ’67 that made him a star. Early that week, Redding, age 26, recorded his soon-to-be megahit song “(Sittin’ On) The Dock of the Bay” that would become his biggest hit song. He was due back in the studio in Memphis on Monday, but not after stops in Cleveland and Madison over the weekend for a couple of shows.

“It was really exciting because Madison had such a small African-American community at the time. For somebody of Otis Redding’s stature to come to Madison, Wisconsin, we were so excited,” Hilliard tells Madison365 in an interview at Goodman Community Center on Madison’s near east side. “We were so elated. We were planning our wardrobe weeks in advance on what we were going to wear and we were planning what dances we were going to do. We were just exploding with excitement about Otis.”

Edith Hilliard at 19 years old: “We were so elated. We were planning our wardrobe weeks in advance on what we were going to wear and we were planning what dances we were going to do. We were just exploding with excitement about Otis.”

Hilliard remembers attending with her good friend, Rosetta Williams. It was Hilliard’s first concert and she was excited. “We had such a small African-American community here … to have somebody of his stature come was huge,” says Hilliard, who was living on Fisher St. on the south side of Madison at the time. “It was a mostly white crowd waiting. Everybody was excited.”

Otis Redding and The Bar-Kays were going to be the headliners that night and The Grim Reapers, a four-piece rock group from Rockford, where scheduled to be the opening band. “They were the band that would become Cheap Trick. They became pretty famous,” Hillard says. “It was an eerie name though – Grim Reapers – looking back at it now and what happened that night.”

An original poster for the concert, designed by William Barr. a sophomore at UW-Madison in 1967,

The Factory was a famous Madison music venue located just off State and Gorham streets in downtown Madison. The two-story brick building is now home to Avol’s Books. Back in the day, it hosted major national music acts like Jimi Hendrix and the Steve Miller Band.

“The Factory was quite a famous place and some major national artists who performed there,” Hilliard remembers.

What did the inside look like?

“It looked like a factory,” Hilliard laughs. “Big open-type space. It looked like a big factory. Nothing fabulous. There was a stage and a huge dance floor.”

Hilliard remembers standing right outside The Factory, in line with her friend, feeling all kinds of anticipation for what the night would bring. This was going to be one of the most memorable nights of her life.

And it was. But in an awful way. Redding’s plane crashed in Lake Monona making their final approach to Truax field on Madison’s east side, which is now Dane County Regional Airport. One of the greatest singers and entertainers of all time was dead at the age of 26.

“Somebody from The Factory did come out and they told us that there had been an accident and there would be no concert. They didn’t tell us that the plane crashed,” Hilliard says. “We had no idea what was going on.”

So, nobody tweeted anything about it that night?

“Haha. It’s interesting when you look back at it now … if we would have had our phones, we would have known everything that happened in an instant,” Hilliard says. “Somebody came out and gave us some news, but it wasn’t all of the news. The next day we found out. In today’s technology, you would have known exactly where it crashed and who was on it and all of the information right away. But we had no idea what was going on.”

Of course, later on, Hilliard would learn exactly what had happened and why the concert was canceled. The plane carrying Redding and most of the Bar-Kays crashed into the icy waters of the Squaw Bay area of Lake Monona a few miles short of its destination. Hillard remembers the newspaper the next morning and seeing the plane emerged halfway in the frozen lake.

“He was such a young man. What a talent he was. Everybody but one person perished,” she remembers.

Ben Cauley Jr. was the only survivor of the 1967 plane crash that claimed the lives of soul singer Otis Redding and four members of the Bar-Kays. He’s pictured here at Monona Terrace’s 40th anniversary celebration for Otis Redding.
(Photo by A. David Dahmer)

That one person was 20-year-old Ben Cauley Jr., a trumpet player, vocalist, songwriter, and founding member of The Bar-Kays. Cauley managed to unfasten his seat belt and grab a cushion before he was flung out from the plane. He clung to that cushion and listened while his good friends died, one by one, in the icy waters of Lake Monona, before he was picked up by a Madison police boat. They couldn’t believe he was alive.

Hilliard and I both were able to meet Cauley at the 40th-anniversary celebration for Otis Redding at Monona Terrace back in 2007. She speaks fondly of the Otis Redding Memorial on top of Monona Terrace. As a volunteer docent, Hilliard has been giving tours of Monona Terrace for 20 years now. She says that she gives a tour about three times a month.

“That’s where I always end my tour – at the Otis Redding site. We sit there and talk about Otis Redding,” Hilliard says. “Every single person is shocked that this is where it happened.”

A trio of marble benches at Monona Terrace’s Rooftop Garden and a plaque commemorating the passing of Otis Redding and his bandmates was unveiled back in 1997. They overlook Lake Monona – and the site of the tragic crash.

“It’s interesting when I take people on tours of Monona Terrace now and I talk about the Otis Redding Memorial, and some of the young people will be like: ‘Who’s that?’ and I’m like ‘Ohhhhhhhhhhhhh,’” Hilliard laughs, clutching her chest. “It crushes me. But it’s a whole other era.

The Otis Redding Memorial on top of Monona Terrace

“However,” Hilliard continues, pausing, “many times while I’m talking they’ve got their phones and they will do some reading while they are walking along and they will say, ‘Ohhhhhh. He was famous!’”

Hilliard looks down at the framed picture I brought her of Otis. Classic Otis. The picture of him smiling, hand on the side of his face for his publicity handout.

“He was a handsome man. So young. So talented,” she says. Long pause, still looking at Otis. “Fifty years. I can’t believe it.”

“How can you even be old enough?” I ask, trying to lighten the mood.

Nineteen-year-old Edith Hilliard

“Riiiiiiight? That’s what I tell my kids all the time,” Hilliard laughs. “I just had my 50-year class reunion for East High School. I can’t believe that it has been that long.”

All these years later, Redding never strays far from Hilliard’s mind or her heart because she’s always talking about him on Monona Terrace tours. But his songs bring her back, too. Right back to 1967. Especially, her favorite song: “(Sittin’ on) the Dock of the Bay.”

“That’s the other thing I always remember is that Otis recorded the song ‘(Sittin’ on) the Dock of the Bay’ that very week!” she says. “It had not even gone live at that point. He recorded it and then he was off. And then his plane crashed on the dock of the bay? That is eerie.”

(Sittin’ on) the Dock of the Bay would become the first posthumous #1 hit in Billboard magazine’s history.

“I really love that song,” Hilliard says. “Every time I hear his voice, it sends me back in time. It makes me happy.”