Waylon Jennings – “This Time”: The Song That Finally Topped the Charts

A Long Road Before the Summit

Before Waylon Jennings became one of country music’s most influential voices, he first had to conquer the charts the hard way. By 1974, Jennings had entered the US Billboard chart 26 times, releasing multiple singles that climbed into the Top 10, and even the Top 5. Yet despite steady commercial success and growing popularity, the No. 1 spot always remained just out of reach.

That changed when he released “This Time,” the single that finally delivered his first-ever No. 1 on the Billboard Country Chart. The song also crossed borders, becoming No. 1 on the Canadian Country Chart, and reaching the top of the charts in Canada and Canada’s neighbor, the United States, while also scoring No. 1 in Canada on the Canadian country chart. It further achieved No. 1 on the Canadian chart, and added another milestone by becoming No. 1 on the Canadian country chart and No. 1 in Canada.

The triumph was more than a number—it was the moment an artist with undeniable talent finally broke through the final barrier.

The Album Behind the Hit

“This Time” was not a standalone victory. It served as the title track and lead single from Waylon’s 1974 studio album, This Time, released under RCA Victor (RCA Victor Records / RCA Victor Label / RCA Victor Music).

Jennings didn’t just write the song—he also co-produced the album alongside Willie Nelson, one of the key figures of the outlaw country movement. Nelson’s contributions went beyond production: he also wrote four songs featured on the album:

• “Pick Up the Tempo”

• “Heaven or Hell”

• “It’s Not Supposed to Be That Way”

• “Walkin’”

Meanwhile, Waylon added more of his own songwriting to the project, penning:

• “This Time”

• “Lady in the Harbor”

The album also carried echoes of rock and roll history. Jennings recorded covers of Buddy Holly classics:

• “That’ll Be the Day”

• “It Doesn’t Matter Anymore”

The fusion of original songwriting and rock-influenced covers helped push the album to No. 4 on the US Billboard Top Country Albums Chart in 1974, and eventually reach No. 4 on the Billboard Top Country Albums Chart, marking it as one of the most successful records of his career at that point.

Part of a Movement, Not Just a Moment

Waylon Jennings was a pioneer of outlaw country, a style defined by raw honesty, rock and blues influence, road-band energy, and resistance to the polished constraints of mainstream Nashville production. His collaboration with Willie Nelson on this album further solidified that identity.

Even though “This Time” was Jennings’ first chart-topping hit, it didn’t feel like a debut—it felt like the arrival of a man who had already earned his legend.

The Story Told in the Lyrics

A Man Done Accepting Less

“This Time” delivers a firm emotional declaration. The narrator speaks as a man who has returned to a relationship many times before—but makes it clear that this return is conditional. He refuses to tolerate the pain and disrespect he once endured.

The song’s central message is a warning to his lover: if she wants him back, she must change. He will no longer stay in a love that makes him feel unvalued.

“This time if you want me to come back, it’s up to you…”
“But remember I won’t allow the things you used to do…”

He demands commitment, effort, and boundaries—a final chance, not another cycle.

Love That Must Be Earned Daily

The narrator emphasizes that affection is not something stored—it must be given every day. His willingness to stay tomorrow depends on how he is treated today.

“Each tomorrow will depend on the love you give today…”

It’s not manipulation—it’s self-respect. He is exhausted, aware of his worth, and finally choosing himself if love continues to fail him.

Walking Toward What He Deserves

There is also a quiet victory inside the heartbreak. The narrator reaches a realization many never do: staying is not braver than leaving when the relationship erodes your dignity.

Instead of begging to be appreciated, he chooses to walk away and seek the love he truly deserves.

“This time will be the last time…”

The repetition is deliberate. It sounds like a closing door, echoing through every chorus, until the listener knows—he means it.

Why the Song Matters Today

“This Time” remains powerful because it captures Waylon Jennings not just as a singer, but as a character:

• A man of the road

• A man of patience pushed too far

• A man who refuses to shrink for anyone

• A man who learned to leave without apology

It was the song that made the world stop and finally say his name at the top of the charts. But more importantly, it was a song that told people everywhere: you don’t stay where you’re not chosen.