The first was when his band Australian Crawl made their debut on Countdown, Reyne singing the band's first single Beautiful People with both arms encased in plaster after being hit by a car.
The second was a memorable parody by The Late Show which sent up his unmistakable (and often indecipherable) vocal delivery - with subtitles.
He gets reminded of both on most days, but reminds AAP that The Late Show also satirised Kylie Minogue, John Farnham, Jimmy Barnes and the Little River Band - some of the biggest names in Australian music.
''I was flattered, to be honest,'' he says. "I thought it was funny - one of the (lyrical) subtitles was 'something about gnocchi'."
Reyne has no reason to feel insecure after a long and successful solo career since Australian Crawl, the band he likes to refer to as his musical apprenticeship.
But at the same time, he knows that apprenticeship set him up for life.
"I was young and it was great. My memories of that band are a lot of driving and a lot of laughing," he says.
Australian Crawl had everything going for them: young, good-looking, a knockabout image, a charismatic lead singer and multiple songwriting talents, with a surf-and-sun sound: California via Victoria's Mornington Peninsula, where the band grew up.
Between 1980 and 1983, they had a memorable run of hits: Beautiful People; The Boys Light Up; Errol; Downhearted; and the Semantics EP which topped the Australian charts on the strength of its lead track, Reckless.
But by then, the band was showing signs of strain.
Drummer Bill McDonough was sacked and his brother Guy, author of Errol and Oh No, Not You Again, died in 1984 of pneumonia after a battle with substance abuse.
By 1986, it was all over. The band never played again. Rhythm guitarist Brad Robinson succumbed to cancer a decade later at 38 - two weeks before Australian Crawl were inducted into the ARIA Hall of Fame.
Forty years later, core members Reyne and lead guitarist Simon Binks are finally reuniting as Australian Crawl for the Red Hot Summer tour - joined by Reyne's younger brother and original drummer David, better known to most as an actor and TV presenter.
Why now?
The first hints something was brewing was in March, when James Reyne and Binks issued a statement announcing a Federal Court challenge to Bill McDonough, who had trademarked the band's name in 1990 - allegedly without consulting other members of the group.
Their lawyers say that amounts to deceptive conduct, arguing when people think of Australian Crawl, they think of the classic line-up of Reyne, the McDonough brothers, Binks, Robinson and bass player Paul Williams - not Bill McDonough alone.
"I've done a lot of press, and no one asks me about Bill," Reyne says drily, remembering a moment when he bumped into the ex-drummer's wife at a bottle shop. ''She yelled out, 'Hey James! Thanks for the royalties!''
AAP approached McDonough for comment, asking whether he was contesting the band's use of the name for the tour, with no settlement having been reached.
His manager, Nathan Brenner, replied: "Our current situation is that this matter is before the court and as such, we can't respond, even though we'd like to."
Reyne insists he bears the drummer no ill will. The band ended more or less amicably: "I've never had a problem with anybody; I just got on with my life."
Nor, he says, does he have any issue with Binks, who appeared on A Current Affair in 2014 in a segment that appeared to pit him against the singer. Binks, who was unavailable for interview, later said he had been misrepresented.
Upcoming tour and legalities aside, Australian Crawl is mostly water under the bridge for Reyne. He sells out venues on his own; had solo hits with Fall of Rome, Hammerhead, a cover (with James Blundell) of the Dingoes classic Way Out West that went to No.2 on the charts.
"Yeah, it was my apprenticeship. Everyone else is going, 'Oh, legendary, classic' … I don't know, it was just a band I was in. Was it that good, really?" he asks rhetorically.
But then, almost in the next breath, he adds: "Pound for pound, I'll go up against anyone. It's a really great rock 'n' roll band, one of the best rock 'n' roll bands in the country."
Not a bad apprenticeship.
12°C