It's hard to choose just twenty of Ed Sheeran's most heartbreaking ballads. The "Thinking Out Loud" singer has made the most romantic break-up songs of our generation, garnering praise from industry greats like Elton John and smashing records for touring and streaming numbers. Unlike famous pal Taylor Swift who prefers to keep things a little closer to the vest, Ed hasn't been shy about the inspiration behind his songs from his biggest hits to his B-Sides. We've decoded Ed's saddest ballads so you can wallow in your feelings while relating to his because misery loves company.
One of Ed's earliest hits is also among his saddest. "The A Team" takes its title from Class A drugs like crack cocaine and heroin, an attempt by Ed to broach the serious topic of addiction with a bit of subtlety. Ed told Billboard the song was inspired by a show he played at a homeless shelter when he was 18, where he was taken aback by the dark stories he heard from the shelter's inhabitants. Ed wrote "The A Team" for a homeless woman named Angel, whose stories of prostitution and begging for drug money can be seen in the song's music video.
Skip "Supermarket Flowers" if you don't want to mess up your mascara. Fans were surprised to learn this much-loved ballad about a mother's death isn't actually about Ed's mother, although it is, sadly, based on a death in his family. Ed explained to Zane Lowe that his grandmother was sick while he was making Divide and passed shortly before the album was finished. His grandfather encouraged Ed to put "Supermarket Flowers," a tribute to his grandmother written from the point of view of his mother, on the album, and Ed now considers it the most special song on the record.
Ed has dated a handful of women since he's become famous (at least, a handful that we know about), but most of his early songs are about one early relationship from his teens. Ed's been open about ex Alice Hibbert inspiring nearly all of Plus, so when he told Just Jared Jr. that the ironically depressing song "Happier" from Divide is about a relationship that inspired most of his first and second albums, it was pretty obvious that meeting Alice's new boyfriend was a tough moment for the ginger crooner.
There's a certain generation of millennials who, no matter how old we get, will always get teary-eyed at even the mention of John Green's novel The Fault In Our Stars. When Josh Boone made The Fault In Our Stars into a slightly-less depressing film, he enlisted a group of artists, including Ed, Birdy, and Charli XCX, to write original songs for the film's soundtrack. Ed told The Hollywood Reporter that "All of the Stars" was inspired by the film as a whole, and that he wanted it to be sad and euphoric at the same time. He also mentioned that he didn't want it to depress people too much, but we can't always get what we want.
We can argue eternally about what Ed's breakout American hit was, but when it was used in a Michael Bay-directed Victoria's Secret commercial (that played roughly five million times an hour, back in the days when we still had to watch cable), there was no denying that Ed Sheeran had finally broken into the mainstream. Ed told Artist Direct that he wrote the song about a relationship that's fallen apart that he's asking to put back together after drinking himself into a dark corner. He wrote the song in twenty minutes because he was feeling so inspired.
Before you start getting any ideas in this politically-charged climate, "Small Bump" isn't about abortion. Ed actually used Instagram Stories to clarify, once-and-for-all, that he doesn't support "Small Bump" being used in anti-abortion campaigns because it doesn't reflect the actual meaning of the song. "Small Bump" was, instead, written in honor of Ed's close friend who experienced a still-birth miscarriage five months into her pregnancy. Like "Supermarket Flowers" and "Nancy Mulligan," Ed wrote "Small Bump" from someone else's perspective. In this case, Ed put himself into the shoes of one of the baby's parents.
Bradley Quinn / Lowden Guitars/Supplied by WENN.com
An underrated Plus deluxe track, Ed wrote "Autumn Leaves" about a dear friend's death, according to the vaguely-reliable Genius. It's a song Ed has rarely sung live, even back in the Plus era, probably because it's one of the most somber tracks of his career. The lyrics aren't exactly subtle, comparing his friend's passing to the dead autumn leaves falling from a tree. Taking them at face-value, Ed wrote this song the day after his friend died, and it's clearly an extremely personal look at how Ed processed his loss.
Ed told News.com every song on Multiply aside from "Thinking Out Loud" is a song grappling with personal demons and that "I'm A Mess" was written at his lowest point. Ed said the song is actually nicer than how he was feeling at the time, but the process of writing sorted everything out for the British songwriter. The song is meant to be self-explanatory, following the dark side of partying with the young, rich, and famous, but some lines are frustratingly opaque. "I'm A Mess" actually features one of the strangest lines in the Sheeran Lexicon, "Put your faith in my stomach," which the singer tweeted was meant to refer to trusting his gut reactions.
Ed's career was built on songs about love and losing love, but like his friend Taylor Swift, Ed's written about more than his romantic exploits. "Afire Love" from Multiply will be a familiar story for anyone who's seen a family member suffer from Alzheimer's or seen The Notebook. The song follows his grandfather's twenty-year struggle with the memory loss disease and how it affected his grandmother through his grandfather's passing and funeral. Ed told Music-News he started writing "Afire Love" two weeks before his grandfather passed away during Christmas not knowing that the patriarch's time was coming.
Another song about familial strife on Multiply, poor Ed has clearly gone through it. The Odyssey thinks "Runaway" is about Ed's father, but we're not entirely convinced that this isn't an "A Team" situation where Ed is telling someone else's story because of Ed's well-documented, healthy relationship with his father, John. To be fair, Ed had his fair share of substance abuse problems during his career, and that sh*t's hereditary. The song includes lyrics about Ed leaving at sixteen to start his music career, so maybe The Odyessy's literal reading of the lyrics about a boy running away from home and his alcoholic father was pretty on-point.
Ed told Fresh 102.7 he wishes he'd kept "I Was Made For Loving You" for himself, but he'd promised Tori Kelly that whatever came out of that fateful writing session would be for her album. Props to Ed for keeping his promises — hopefully, performing on the track as a duet alongside Tori dulled the pain a little. "I Was Made For Loving You" is about the fearful part of starting a new relationship with the knowledge that a fast, strong love opens you up to the possibility of a broken heart.
Seeing Ed Sheeran live is a magical experience. It's just Ed, a guitar, and a loop pedal, and in lieu of the hyper-polished performances preferred by his contemporaries, Ed takes time to open up to the audience about his songwriting and how his fans' favorite hits came to be. For "Kiss Me," Ed told a Nashville crowd (captured via YouTube) that he wrote the song for his godparents' wedding. His father's best friends had been close for ages, both marrying other spouses and eventually divorcing their respective partners. After forty years of friendship, they realized they were in love, and his godfather proposed. This ballad really wouldn't be sad at all if Grey's Anatomy hadn't used it during a particularly upsetting scene on season nine.
Not to be confused with the lighthearted "New Man," Ed managed to turn white rapping into a bluesy, heartwrenching stream of consciousness ballad dragging his ex-girlfriend for filth. The lyric-heavy track has a lot to wade through, but lines referring a relationship that ended just as his career took off and his girlfriend left for college (read also: "U.N.I.") make it obvious that this is another song about Alice. Ed seems upset about Alice's new relationship, which began suspiciously close to their breakup, and realizes that his career is the reason they didn't work out. Do you think Alice is getting a little tired of having a relationship from seven years ago continually made into chart-topping songs?
In case anyone still wasn't sure if Alice cheated on Ed, may we draw your attention to Multiply's "Shirtsleeves"? Ed originally tweeted the lyrics in 2011, when literally all of his songs were about Alice, and the lyrics allude heavily to a cheating significant other. "I'll hold you/And you think of him/And pretty soon you'll be floating away" certainly sounds like his lady friend is thinking of another man, and lines like "I'll never trust you again" and "I'm captain of the sinking boat" just hammer in the idea that Ed was hanging onto a relationship that had fallen apart due to infidelity. Our best guess is that "Shirtsleeves" is about Ed comforting his love after she's admitted to cheating.
Supplied by WENN.com
"Friends" hits close to home for anyone in an undefined relationship, but we weren't sure what Ed's inspiration for the hashtag relatable content was until we read about a radio interview he did shortly after his failed romance with Ellie Goulding. Ellie was once known as the singer of 2010 hit "Starry Eyed," but she'll probably go down in history as the girl who cheated on Ed with Niall Horan while they were staying in the same hotel because America loves its gossip no matter the fact that no one knows if it's actually true or now. Anyway, in Ed's radio interview, he told Click 98.9, "Normal people don't hold hands if they're just friends." That could literally be a line from "Friends," which appeared on the Don't EP, featuring the very song that started the firestorm of cheating accusations.
"Dive" is highly underrated, if only because it features a mystery solo by Eric Clapton under the Angelo Mysterioso pseudonym. All of the love songs on Divide are about Ed's now-wife Cherry Seaborn, he told GQ, so we can go out on a limb and assume she did mean it when she called him baby. This song about Ed's early fears about how easily he could fall in love with Cherry was co-written by Julia Michaels, who spoke about a panic attack she had during the writing process to Billboard and had to return another day to finish the song with Ed.
The newest Ed song on this list, "Best Part of Me" featuring Yebba, is also about his new wife, and he opened up to Charlamagne Tha God about how much Cherry contributed to No. 6 Collaborations Project. In addition to suggesting the Justin Bieber feature on "I Don't Care," Cherry's love inspired "Best Part of Me" because of how amazed Ed is that she sees all of his flaws and wants to be with him anyway. Ed continued, saying that he constantly wakes up and wonders why she chose to be with him. We stan a humble global phenomenon.
"Lego House" was a Big Moment for the then-unknown Ed Sheeran, and not just because Rupert Grint agreed to star in its music video. Capital FM says the mellow melody is about a relationship that's slowly deteriorating that Ed is trying to mend so his partner doesn't get hurt. Since this song is also definitely about Alice, we know that Ed's career and her departure for uni caused a major strain in their relationship that wasn't able to be fixed, but this was the first in a long string of hits about the failing relationship that made Ed a star. Bit of a Faustian exchange, that one.
Ed told Music-News that "One" was the last song he ever wrote about the relationship that inspired Plus so, yes, this is another song that's probably about Alice. Something tells us that wasn't the healthiest relationship. Multiply was Ed's first album following his debut, and he said that writing "One" was like his closure for both Plus and for his relationship. He also said that it's the only song on Multiply about that relationship, but since "Shirtsleeves" was written while he was with Alice, "The Man" was about the aftermath of their breakup, and he's later said a few songs on his second album were about her, we're thinking he's not always the most reliable narrator.
Sometimes, long-distance relationships can hurt worse than the messiest breakups. It's a different type of pain, like a strange prolonged ache with a heaping spoon of doubt, but Ed's hit "Photograph," which he wrote in ten-minutes with Johnny McDaid from Snow Patrol, is a tender ballad of hope for his long-distance GF, who at the time was Scottish singer Nina Nesbitt. Once we learned the other song on Multiply about Nina, cleverly titled "Nina," is about how Ed's never coming home and their relationship is over, "Photograph" started hitting a little different.