Photo by Jemal Countess//Getty Images

Chicago-born soul queen, [lastfm link_type="artist_info"]Jennifer Hudson[/lastfm], may be madly in love with her husband, but the 29-year-old singer has seen enough heartbreak and tragedy with her mother, brother, and nephew’s murders to last her a lifetime.

However, when it comes to love, most of Hudson’s songs are more on the positive tip. We did find Five Jennifer Hudson Songs About Heartbreak that we absolutely love, including a heart-wrenching cover of [lastfm link_type="artist_info"]Gladys Knight and the Pips[/lastfm]‘ “Neither One of Us (Wants to Be the First to Say Goodbye).”

Hudson has been through a lot, which makes her live performances even more magical and powerful, especially her free streamingLive on Letterman concert from the Ed Sullivan Theater on June 13th at 9 PM ET. You can watch the entire concert, live right here!

5. “Why Is It So Hard”

Photo by Larry Bussaca//Getty

Sometimes you can still be with someone in a relationship, but they make you sad and break your heart a little more each day, like Jennifer Hudson’s lover in “Why Is It So Hard”:

Doesn’t make sense irrational to me/I’m still around though I can’t believe one word that you say/No it don’t make no sense I’m always crying/But I’d cry oceans if you ever went away/But I could never ever feel like this/When the words I love you leave my lips/I mean it when I say I just hate how difficult you make it