Gerry spent 2021-2022 playing his biggest shows to date. His 350,000-capacity UK and Ireland tour, originally due to happen in 2020, included shows at Birmingham and Manchester Arenas, London’s Alexandra Palace, the 25,000 capacity Malahide Castle, Dublin, and Musgrave Park Stadium, Cork. He also headlined at Swansea’s Singleton Park, the second biggest show ever held in the Welsh city, [51] and set the record as the first artist to sell out three headline shows at the Belsonic, Belfast, playing to over 60,000 fans [52]. [53]

In this music game, or in any game, you've got plenty of opportunities to make the wrong choices. ‘Lullaby’ is a projection of my future if I started believing my own hype, started going to all the parties that I get invited to and just became another industry…what’s the word I'm looking for…c*nt. It's a sarcastic take on what musicians are supposed to be. It's also about me as well—there’s my own fears mixed in with it. In 10 years time, if I became a caricature of myself, and became a cliché music person, that would be my outlook. And if it ever gets to that point, then just ‘Sing me to sleep/Sing me a love song’—which is just put me to sleep.” His debut album Erratic Cinematic, released in Septemner 2017, was the definition of a slow burner. Without any major label support, the making of the album was funded by fans through PledgeMusic and put out through his own label, called Little Runaway. Promotion consisted solely of performances at gigs and festivals; and as the venues got bigger, awareness and sales of the collection grew. MORE: The Official Top 40 biggest albums of 2020 so far Brown, Steven (5 May 2023). "Gerry Cinnamon announces release of live Hampden album alongside new music". GlasgowLive . Retrieved 24 July 2023. a b c Geddes, Jonathan (20 July 2015). "Castlemilk singer Gerry Cinnamon is a hit at T in the Park". Daily Record / Rutherglen Reformer . Retrieved 7 January 2018.Sun Queen: "UK Independent Chart Positions". Official Charts. 18 October 2019 . Retrieved 18 October 2019.

Where We're Going: "UK Independent Chart Positions". Official Charts. 27 March 2020 . Retrieved 27 March 2020. The ARIA Report: Week Commencing 27 April 2020". No.1573. Australian Recording Industry Association. 27 April 2020. {{ cite magazine}}: Cite magazine requires |magazine= ( help) The Bonny": "Official Scottish Singles Sales Chart Top 100". Official Charts Company. 6 December 2019 . Retrieved 7 December 2019. Live at Hampden Park: "Scottish Albums Chart". Official Charts Company. 21 July 2023 . Retrieved 22 July 2023.It’s a kind of ode to my hometown, about people that I've grown up with that are ridiculous characters. I play it all over the world, and no matter where I play it, you've got people singing it about their hometown. Now I dedicate it to wherever I am—it went from Glasgow and became something else, which is beautiful. It doesn't matter where I go, I still carry all the scars, the good and the bad, from where I was brought up. Because I love it and hate it at the same time. ‘No’ the best place, but there’s diamonds in the mud.’ No matter where you're from, I think people can relate to that.” In 2020 his second album, The Bonny, reached number one on the UK Albums Chart and became the third biggest selling UK album released that year. [4] Dunworth, Liberty (5 May 2023). "Gerry Cinnamon announces new live album, confirms work on next record". NME . Retrieved 24 July 2023.

In October he was presented with a 'Great Scot Award' for entertainment, following previous winners of the category such as Paolo Nutini and Kevin Bridges. [26] [27] In December it was confirmed he would be returning to TRNSMT in 2018, this time on the main stage. [28] [9] [10]What Have You Done’ is watching my mate fall foul to the dangers of the party. Watching somebody that I cared about become someone else in front of my eyes—and trying to stop it. At the time I thought I was writing it about him, but I realized well after I'd written it that I was really singing about myself.” Lennon, Holly (28 September 2017). "Castlemilk star Gerry Cinnamon tops the charts with debut album". Evening Times . Retrieved 7 January 2018.