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Starting with a 1966 double bill of Jefferson Airplane and the Paul Butterfield Blues Band, Bill Graham began to occasionally rent the venue for larger concerts that his nearby Fillmore Auditorium could not properly accommodate. After closing his New York City venue known as the Fillmore East in 1971, he began to hold regular weekend shows at Winterland. Various popular rock acts played there, including such bands and musicians as Bruce Springsteen, The Rolling Stones, The Who, Cream, The Doors, Jimi Hendrix, Led Zeppelin, Lynyrd Skynyrd, Allman Brothers Band, The Grateful Dead, Jethro Tull, Rush, Genesis, Jefferson Airplane, and Elvis Costello, the latter in support of his Armed Forces album. A great number of the best-known rock acts from the 1960s and 1970s played Winterland or played two blocks away across Geary Boulevard at the original Fillmore Auditorium. Peter Frampton recorded parts of the 4th best-selling live album ever, Frampton Comes Alive!, at Winterland. The Grateful Dead made Winterland their home base, and The Band played their famous last show there on Thanksgiving Day 1976. That concert, featuring numerous guest performers including Neil Young, Eric Clapton, Bob Dylan, Joni Mitchell, and many others, was filmed by Martin Scorsese and released in theaters and as a soundtrack under the name The Last Waltz. Winterland was also host to the Sex Pistols' final show on January 14, 1978.

During Winterland's final month of existence, shows were booked nearly every night. Acts included The Tubes, The Ramones, Smokey Robinson, Tom Petty and the Heartbreakers, and on December 15-16, 1978, Bruce Springsteen & the E Street Band. Springsteen's December 15 show was simulcast on local radio station KSAN-FM and Springsteen historians consider that show one of his most legendary. Winterland closed on New Years 1978/79 with a concert by the Grateful Dead, New Riders of the Purple Sage, and The Blues Brothers. The show lasted for over eight hours, with the Grateful Dead's performance — documented on DVD and CD as The Closing of Winterland — lasting nearly six hours itself. The final show was simulcast on radio station KSAN-FM and also broadcast live on the local PBS TV station KQED. Winterland was eventually torn down in 1985, and was replaced by apartments.