Music has always been a big driver in Perry Gilman’s life. While in college at Concordia University in Montreal, the Madison House agent started his foray into music by booking shows on the student events committee, hosting a weekly radio show, and holding four DJ residencies during his time as an undergrad.

“Luckily, I had a chance once in a while to DJ and open up for artists like Kid Cudi, DJ AM, Justice, Busy P on some of their first shows in Montreal,” Gilman told Amplify. “I was super intrigued by these artists lifestyles and the business behind them.”

Gilman moved to Toronto and gained additional experience in publishing, music supervision and TV while completing his second degree at The Harris Institute.

“After gaining experience in different fields, I realized that I loved the live show,” Gilman said. “While being entrenched in the music scene in Montreal, I felt I knew how to interact with talent. I loved being around creative, passionate and forward-thinking artists. I didn’t really like promoting shows. I felt I had a better understanding of where the artist should be playing. I started to research Canada as a whole and soon become an agent.”

Gilman spent the next six years working at The Feldman Agency, one of Canada’s largest agencies.

While seeing some of his roster grow exponentially in the U.S., Gilman felt it was time to expand outside the borders of Canada and begin booking in the States.

”Having a strong relationship with Madison House for years, we shared many artists across the border while I was at TFA. They offered me an opportunity to open their Canadian leg of the company and build a team in Toronto booking both U.S. and Canada,” Gilman said. “We’ve grown exponentially and expanded our U.S. roster and Canadian business across clubs, colleges, corporates and had many perform and headline some of the largest festivals this country has to offer.”

It has been three years since Gilman joined Madison House and Amplify caught up with him to learn about five shows that have wowed him over the years.

Linkin Park at Parc Jean Drapeau in Montreal

July 20, 2003

I’ve seen Linkin Park a ton of times and thought it would be best to date back to the first time. This was my first larger than a club concert I went to. I was 17. Linkin Park was and still is one of my favorite bands of all time. At this show, they were supporting Limp Bizkit and Metallica! Wild! My buddy crowd surfed. I couldn’t find him for about three hours. I drank beer and watched the entire show solo and sang every word.

Red Hot Chili Peppers at Portman Road in Ipswich, Suffolk

July 3, 2006

After graduating university, three of my best friends and I went backpacking across Europe for a few months. This concert was the anchor date of our entire trip. There were so many epic things that happened on our 2 hour trip from London to the stadium that truly only belong in a movie. But Chili Peppers killed it as always. This was the last time I saw John Frusciante live. Flea was naked the entire show and we made it home alive!

Daft Punk at The Bell Centre in Montreal

Aug. 7, 2007

I went to this show with a few DJs in Montreal. We were all obsessed with Daft Punk. We played a lot of their music. They were huge inspirations to us- their gimmick, brand and music were just insane, in my opinion. They took mash-ups to a whole other level with their Alive album. They also took production at concerts to another extreme on this tour with their pyramid stage.

The Weeknd at The Ale House in Kingston, Ontario

March 15, 2012

Before The Weeknd did his first hometown show a few months later, a team of agents at The Feldman Agency booked about 8-10 closed campus shows in surrounding college markets near Toronto. I was involved in this particular show and I remember hanging with The Weeknd backstage just after his performance and said, ‘You are going to be one of the biggest artists on the planet one day.’ Working with him was short lived as he ended up signing with one of the big four soon after. It was still cool to witness the beginning. He was one of my early A&Rs. I’m very happy for his management team. I worked with them on other artists they used to manage early on and witnessed their exponential growth over last 5+ yrs.

Drake at Molson Ampitheater in Toronto

Aug. 4, 2013

As you all know, Drake is one of Toronto’s number one ambassadors and reps this city more than anyone. On August long weekend every year (Canada’s Civic Holiday), he presents OVO Festival with loads of surprise guests. That year he brought out TLC, Big Sean, J. Cole, Diddy, Ma$e, Kanye West, and more. The show’s production gets bigger and better every year. It’s always a weekend to look forward to, but this one stood out the most. This past year they even built a mock CN tower on stage!