21 Sad Country Songs That Were Big Crossover Hits

It’s easy to assume that songs become huge crossover hits because they’re fun, upbeat and danceable.

Shaboozey‘s “A Bar Song (Tipsy),” Morgan Wallen and Post Malone‘s “I Had Some Help” and Florida Georgia Line‘s “Cruise”: They all became cross-genre smashes because of their feel-good, song-of-the-summer vibes.

But it’s not always a fun song that hits the top of the Billboard Hot 100. We’ve got 21 songs that prove that heartbreak can make a huge crossover hit, too!

Most recently, Ella Langley proved ’em all wrong with her genre-spanning, history-making hit “Choosin’ Texas”: A song that became a massive cross-genre success despite its theme of heartbreak and its traditional country production.

But Langley is far from the only performer who’s accomplished this feat with a breakup song. In fact, she only ranked No. 14 on our list of sad songs that became huge crossover hits.

For this list, Taste of Country looked at the full history of country music, including the busy year of 1975: That’s when a whopping six pop-country songs made it to the top of the Billboard Hot 100.

Read More: 18 Sad Country Songs That Sound Happy

We’ve selected the all-time best and biggest sad crossover hits, including modern-day classics by Luke Combs and Morgan Wallen as well as all-time greats from Skeeter Davis, Freddy Fender and Ray Charles.

Keep scrolling to see the full list, including our pick for the all-time best sad crossover smash. This song, released by a country icon, was so popular that when an artist from another genre covered it, her reworked pop rendition became a diamond-certified song in its own right!