This year has already been bittersweet for fans of pioneering hip-hop group, De La Soul. There was the recent death of group member David Jolicoeur, aka Trugoy, which came on the heels of the announcement that the group’s first six albums would finally be available on streaming platforms.

So why the decades-long wait? The answer is sampling. Their 1989 debut album, 3 Feet High and Rising, for example, used more than seventy samples. And while they were cleared for LPs and cassettes (well, mostly, but we’ll get to that), no one saw the streaming age coming.

“Once the whole age of digital music came into play, new deals needed to be cut for those entire albums,” De La Soul’s Kelvin Mercer, aka Posdnuos, told the BBC. And the record company didn’t want to deal with it, he continued. “They’re like, ‘Is it worth it?’ They’ve got to go through almost every song with a fine comb to make sure this sample or that sample was cleared.”

While sampling is one of the big legal hurdles musicians often have to clear, it’s not the only one. And some of those hurdles are so high, placed so perfectly, that sailing over them (or crashing into them, as the case may be) changes the whole race. As lawyer and journalist Victor Li writes, “Occasionally, a band or artist will be involved in a lawsuit so groundbreaking and important that it will set a precedent.”

Sample clearing was an issue from the beginning for De La Soul. Their song, “Transmitting Live From Mars” used twelve seconds from a Turtles song, which, as ethnomusicologist Wayne Marshall explains, ended “in a $1.7 million settlement in 1989,” and “sent a chill through the hip-hop world and a buzz through the business world.”

A whole new economy was created following the suit. “Publishing companies…have instigated hundreds of suits against hip-hop labels, many of them retroactive,” Marshall writes. As Li explains, “Now, there are companies whose main purpose is to obtain copyright clearance for samples.”

The sampling landscape was something new for music and the law, but old familiar genres still faced their share of legal complications. Former member of the Beatles, George Harrison, found himself part of a plagiarism claim in 1971. His song, “My Sweet Lord,” from his solo album, All Things Must Pass, “became the subject of intense litigation for more than 20 years,” Li writes. Bright Tunes Music Corp. sued Harrison’s publishing company, alleging Harrison’s song “copied the melody and song structure of ‘He’s So Fine’ by the Chiffons.” Though Harrison was familiar with the song, he claimed he came up with his independently.

As part of the case, Li writes, “Harrison testified on his own behalf and even brought his guitar to court to show how he had composed ‘My Sweet Lord.’” Even so, he ended up losing, and was ordered to pay $1.6 million. But in a Law & Order-worthy twist, Harrison’s former manager, Allen Klein, bought the rights to “He’s So Fine,” and then sued Harrison so that Klein could collect the judgment amount. The case wouldn’t be resolved until 1998, but its legacy continues. According to Li, “the long-running case significantly expanded the scope of copyright infringement law.”

In maybe the oddest case of plagiarism, former Creedence Clearwater Revival singer, John Fogerty, was sued when his old label, which held the rights to CCR’s catalogue, sued him because his song “‘The Old Man Down the Road’ sounded too much like the Creedence song ‘Run Through the Jungle’ (Fogerty had written both songs).” Fogerty won and, after a change to the 1976 Copyright Act, was able to recover his attorney fees.

In her trio of lawsuits in the early 1990s, singer Martha Wash was able to reverse her erasure from the industry. After being part of 1970s group, the Weather Girls, Wash became an in-demand session singer and was often asked to provide vocals for various projects. When the albums and videos for the songs were released, however, “her name was nowhere to be seen,” Li writes. It happened a third time with the huge 1990 hit, “Gonna Make You Sweat” by C+C Music Factory, and Wash again sued. Not only was she not credited, but “a model/singer lip-synced to Wash’s vocals on the video.” This, and cases like it, led to the changes in the law to ensure that artists were properly credited for their contributions.

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