For as long as they’ve been around, large-scale, outdoor music festivals have been a prime location for a band to try to create a special moment. Aerosmith capitalized on just such a moment during the U.K.'s Monsters of Rock festival at Castle Donington on Aug. 18, 1990, bringing up Jimmy Page for a thrilling two-song jam.

Growing up around Boston, Aerosmith were always big time Led Zeppelin fans. So much so, that singer Steven Tyler was fine with it when his date left him for one of his heroes.

“In ’69, I saw Zeppelin at the [Boston] Tea Party,” Tyler wrote in his memoir Does the Noise in My Head Bother You. “When the band came offstage, I went back to say hello to the guys, ’cause [Aerosmith road manager] Henry Smith was working for [John Bonham], and who do you think comes walking out of the dressing room on Jimmy Page’s arm? [Tyler's girlfriend] Lynn Collins. She was a genuine, high-class girl-about-rock-’n’-roll-town. I thought to myself, 'If I was gonna lose her, might as well be to a legend like Page.'"

Over the ensuing years, Page became friendly with the members of Aerosmith, and a 1990 trip to the U.K. set up their memorable on-stage collaboration.

Listen to Jimmy Page Jam With Aerosmith

“I travelled with Aerosmith in their tour bus to and from the show,” Page wrote in an On This Day entry on his website. “All of the time on the bus was spent chatting and exchanging stories and at one point Steven played me the current Red Hot Chili Peppers album, and there was much discussion and enthusiasm about music on that journey.”

Page jammed on the blues classic “Train Kept A Rollin,’” which he'd played extensively going back to the Yardbirds era and the earliest days of Led Zeppelin. He also helped end the set with a rousing performance of Aerosmith's “Walk this Way.” “It was a night when we really rode the wave of the crowd’s incredible energy,” Joe Perry recalled in his own biography, Rocks.

Two nights later, Jimmy Page sat in again at the intimate Marquee Club in downtown London – this time with an expanded set list. Page collaborated on “I Ain’t Got You,” by the Yardbirds, “Red House,” by Jimi Hendrix, Led Zeppelin's “Immigrant Song” and an encore of “Train Kept a Rollin’.” Outside of his tryout with the Page, John Paul Jones and Jason Bonham many years later, these couple of shows would be as close as Steven Tyler ever came to fronting Led Zeppelin.