Merle Haggard has weathered some rough times. He was a ditch digger, a short-order cook, a truck driver and a laborer in the oil fields around Bakersfield. The legendary country musician also has served several jail sentences, including one where he spent his 21st birthday incarcerated in San Quentin Prison, an experience he recalls in his classic hit “Mama Tried.” But Haggard says the worst experience in his life was when he and his good buddy Willie Nelson moved to Branson, Mo. in 1990 to run and perform at a theater there.

Known to some as a family-friendly version of Las Vegas, the small city and tourist destination is also known for its theaters, which in most cases present shows by former country music hit makers. “I did a year down there,” Haggard says. “It’s kinda like being in prison.”

Haggard, who now lives near Redding, recalls that he and Nelson didn’t know how the tourist business in Branson worked when they decided to set up shop. “A guy like Willie and I, we thought we could go down there and kill ’em,” he says. “Well, we went down there and killed ’em all right. Ha ha. Learned a good lesson.”

What Haggard and Nelson discovered was that most visitors to Branson picked out the shows they wanted to attend in advance and bought tickets for them months before coming to the town. Without having advance bookings, Haggard and Nelson were playing to a half-full house twice a day and fighting absurd amounts of congestion to and from the theater. “It was the most horrible thing I ever did in my life,” Haggard says. “We played two shows a day, and we spent three hours going to work and three hours coming home. And we only lived a mile and a half away.”

It’s unsurprising that Haggard and Nelson did things their own way when moving down to Branson – the two country music outlaws always have flouted convention. Early on in his career, Nelson moved to Nashville but was not embraced by the country music establishment because of his distinctive voice and phrasing. Though Nelson songs, including “Crazy” and “Hello Walls,” became hits for other country artists, he became so frustrated with the music scene that he temporarily bowed out in 1972 to become a pig farmer in Austin.

When Nelson re-emerged in 1973, it was with a blend of country, rock and folk music filtered through an outsider’s perspective that would become a cornerstone of the burgeoning outlaw country movement. While some of Nelson’s most popular work has been his outlaw country material, he never has been content to rest in just one genre. In 1978, Nelson released Stardust, a collection of pop standards that set the precedent for more recent albums like Rod Stewart’s The Great American Songbook and even Merle Haggard’s 2004 CD Unforgettable. Stardust was predicted to be a flop because it diverged from Nelson’s country sound, but it spent almost a decade on the country charts. Since then, Nelson also has dipped into an atmospheric Tex-Mex sound on 1998’s Teatro and experimented with a mix of country and reggae on 2005’s Countryman.

While Nelson has long stretched the boundaries of country music, Haggard has raised a ruckus by writing provocative songs within them. His most-argued-about number is surely his 1969 hit “Okie From Muskogee,” which begins with the lines: “We don’t smoke marijuana in Muskogee/ We don’t take our trips on LSD.” It’s been often debated whether the tune is a hippie-baiting number or a satirical look at a conservative mindset. One thing is for sure: Haggard is not going to give a definitive answer about his intentions. “Well, there’s a lot of different meanings to it,” he says. “It’s not clear exactly what we are saying, and then again it’s very clear. There’s probably five messages in it. I understand one or two of ’em.”

With his 1970 hit “The Fightin’ Side of Me,” which seems to jab at Vietnam protestors, Haggard would appear to be defiantly conservative, but a look at his catalogue proves that the singer/songwriter is truly an unpredictable voice. In 1970, around the same time of the “Fightin’ Side of Me,” Haggard recorded a song about an interracial couple and colorblind love. Just last year, Haggard debuted a pro-Hillary Clinton number titled “Hillary” with the lyrics: “Let’s put a woman in charge.”

Haggard simply believes times are different from when he wrote songs like “Okie from Muskogee.” “The world has changed,” he says. “What used to be a Republican is now a Democrat and vice versa. What used to be America now more resembles right before the fall of Russia. This country doesn’t resemble the one that was in place when I wrote those songs.”

Regardless of his political viewpoints, Haggard clearly likes to push people’s buttons. “I guess it’s the mischievousness of my personality,” he says of his reason for creating confrontational material. “I love to touch on subjects with people that raise an eyebrow.” Later, he adds a succinct point about how artists can garner interest for their work. “I don’t think you can get somebody’s attention if you don’t have something to say,” Haggard says.

One thing Haggard has always raised his voice about is his love of old country music artists. The country icon has cut a couple of tribute albums to past country greats including 1970’s A Tribute to the Best Damn Fiddle Player in the World (Or My Salute to Bob Wills) and his 2007 double CD collaboration with Nelson and Ray Price titled Last of the Breed, which features covers of songs by old country acts including Harlan Howard and Lefty Frizzell. Haggard says that music these days is so perfect you no longer “hear any mood or any human factor.”

“It was raw,” he says of the old stuff. “It was real. To me, that was more appealing.”

It also seems to be one reason why Haggard and Nelson are such great friends. Haggard says he first met Nelson at a Nashville poker game in 1964, which was also attended by other country music heavy hitters like Porter Wagoner.

“Music sort of brought us together as friends,” Haggard says. “He and I both agreed on a lot of things about music, who was the best guitar player and stuff of that nature.”

Now, the two country music legends are scheduled to perform at Monterey’s Golden State Theatre just two days apart. Nelson plays this Sunday behind his latest release Moment of Forever, a truly mixed bag of an album that includes the novelty number “The Bob Song” penned by Big Kenny of the contemporary country duo Big & Rich and the poignant Randy Newman song, “Louisiana.” Haggard visits town Tuesday on the heels of releasing his latest CD, The Bluegrass Sessions, the first bluegrass album of his career.

Even though Haggard and Nelson are known for their collaborations together – including their hugely popular 1983 duets album Poncho & Lefty – Haggard says the two have no plans to drop in to play with one another at the upcoming Monterey shows. Rather, he says, the two will wait to perform together a few nights later in Reno, where they also will be able to sit down with each other at a poker table.

WILLIE NELSON plays 8pm Sunday, Feb. 10, at the Golden State Theatre, 417 Alvarado St., Monterey. Sold out. 372-3800.

Merle Haggard plays 8pm Tuesday, Feb. 12, at the Golden State Theatre, 417 Alvarado St., Monterey. $59-$99. 372-3800.