"That's What It's Like to Be Lonesome" is a song written and recorded by American country singer-songwriter Bill Anderson.

It was released as a single in December 1958 via Decca Records and became a major hit.

A similar version was released by American country artist Ray Price the same year via Columbia Records.

"That's What It's Like to Be Lonesome" was recorded at the Bradley Studios, located in Nashville, Tennessee.

The sessions were produced by Owen Bradley, who would serve as Anderson's producer through most of years with Decca Records.

"That's What It's Like to Be Lonesome" was released as a single by Decca Records in December 1958.

It spent a total of 17 weeks on the Billboard Hot Country and Western Sides chart before reaching number 12 in February 1959.

It became Anderson's first major hit as a music artist and his first charting record.

It was not first released on a proper album. However, seven years later, it appeared on his compilation From This Pen.