Celebrate Willie Nelson’s 90th Birthday(s) All Weekend Long With A Look Back At His Storied Career

Willie Nelson turns 90 years old on either Saturday or Sunday, or both, depending on who you ask. The outlaw country legend was born on April 29, 1993 in Abbott, Texas. Maybe. Kind of.

Nelson was born so close to midnight that the hospital staff didn’t get his paperwork completed until the next day. So, even though his birthday is actually on the 29th, it’s technically on the 30th.

There has always been some confusion around the exact date of his birthday, but Nelson found a simple solution. He celebrates on both days every year!

This year, which marks Nelson’s 90th year of life, will be no different!

Nelson is hosting a two-night birthday concert at the Hollywood Bowl. Musical guests include Chris Stapleton, The Lumineers, Snoop Dogg, Kacey Musgraves, and The Chicks, among others.

As Willie Nelson looks head to 91, let’s look back at his best moments from the last nine decades!

Nelson, who may be the most widely-beloved figure in country music, released his first album in 1962. He has put out more than 50 (!!) solo studio albums in the 60 years since, and that doesn’t include his singles or time with The Highwaymen.

In addition, Nelson has more than 50 appearances on his filmography. It is often forgotten that he appeared in Austin Powers, The Dukes of Hazzard, Zoolander 2 and Miami Vice, among countless other T.V. shows and movies.

All of this goes to say that there isn’t anything that Nelson can’t do or hasn’t done. The legacy of ‘The Redheaded Stranger‘ will live forever.

While everybody knows Nelson’s song ‘On The Road Again,’ and his iconic look does not go unrecognized. However, there is a lot about Nelson that most people may not know!

Nine fun facts about Willie Nelson on his 90th birthday:

1. ‘On The Road Again’ was written on a barf bag.
   • Speaking of Nelson’s most-famous song, it started out as ink on a vomit bag. He, Sydney Pollack and Jerry Schatzberg were on a plane together, when Nelson was asked if he had any ideas for a song that could be on the movie ‘Honeysuckle Rose.’ After getting a general direction from Pollack, the lyrics started to flow and Nelson wrote it all down on his backseat barf bag!
2. Nelson began his career at the age of nine with a polka band, and his grandmother didn’t approve of the drinking that went on during shows. He wrote his first song at seven years old!
3. He made one of his albums just to pay off the IRS.
   • Nelson found himself in some serious debt in the 1980s and was on the hook for $32 million in unpaid taxes. As a direct result, he released the album ‘The IRS Tapes: Who’ll Buy My Memories’ and paid back all of his debts through proceeds from the album, and by auctioning off some of his assets.
4. Before he became a full-time musician in the 1950s, Nelson worked as a disc jockey, cotton picker and Bible salesman.
5. Nelson paid $14,000 to buy out his contract in 1972 and retire. His retirement didn’t last long, clearly.
6. He has been playing the same guitar for more than 50 years.
   • Nelson started playing his beat-up Martin acoustic ‘Trigger,’ which he named after Roy Rogers’ horse, in 1969.
7. Nelson served in the military with Johnny Cash at Lackland Air Force Base in San Antonio, Texas. His service was cut short at just nine months because of an ongoing back issue.
8. One of Nelson’s nicknames, ‘Booger Red,’ is as literal as it gets.
   • Nelson recited a poem for his first-ever public performance at five years old and was so nervous that he picked his nose until it bled.
9. He once ran into a burning house to save his weed.
   • Back when Nelson was living in Nashville, he arrived home to discover that his house was on fire and burning to the ground. There was little hope of saving a lot of the things inside of the home, like the one hundred+ tapes of unreleased songs that were lost.
   • Inside Nelson’s house was a pound of “Colombian grass,” as he puts it. Scared that a fireman would find his stash and turn him over to the police, Nelson ran back into the burning building and saved his flower.

Nine legendary performances by Willie Nelson on his 90th birthday:

Grand Ole Opry — 1965

Nelson looks very different today, at age 90, than he did at age 32. His medley of hits at the Grand Ole Opry, a weekly American live country music performance and broadcast show in Nashville, shows a side of his career that may have since been forgotten over the years.

The medley includes:

• Hello Walls
• Funny How Time Slips Away
• Night Life
• Crazy

The Willie Nelson Special — 1986

One of the most famous songs of all-time, ‘Georgia On My Mind’ was first released in 1930. It has been covered countless times, but Ray Charles and Willie Nelson’s versions are the most famous.

During a T.V. special in 1986, they got together at the piano and sang it together.

The Midnight Special — 1980

Nelson got his big break in 1975 with his album ‘The Red-Headed Stranger.’ From that album, his song ‘Blue Eyes Crying in the Rain’ became his first No. 1 on the country music charts.

His performance on ‘The Midnight Special,’ the original late night concert show, was a very big deal.

Woodstock — 1999

Much of the 1999 Woodstock music festival is marred by riots, violence and poor conditions, but not all of it was bad! Nelson’s hour-long set had the entire place in good spirits before things turned sour.

Outlaws and Angels — 2004

Nelson brought out a celebrated group of guests for his live album recording at The Wiltern in Los Angeles on May 5, 2004. Toby Keith and Merle Haggard came out to cover a Townes Van Zandt classic.

The Porter Wagoner Show — 1965

RCA artists like Nelson were regularly featured on ‘The Porter Wagoner Show,’ a syndicated musical variety show filmed in Nashville from 1961 to 1980. His performance from 1965 serves as another great look at the pre-bandana era.

The Late Show — 2018

One of the coolest things that Nelson has done during his career is release an entire album dedicated to Frank Sinatra. The outlaw country artist put his own twist on the famous crooner’s greatest hits.

NBC Primetime Special — 1988

Although ‘Stardust’ was originally written and performed by Hoagy Carmichael, it became one of Nelson’s biggest hits during the transitional era after the clean cut and before the braids. His performance of the song went on to win a primetime Emmy Award for ‘Outstanding Sound Mixing for a Variety or Music Series or Special.’

Farm Aid — 2022

Very few musical artists have been able to perform into their 80s and 90s. Nelson is one of them.

Here he is signing an emotional version of what might be his most famous song.

Just to compare, Nelson sounded the same in 2022 as he did back in the day!

Age is but a number to Willie Nelson, who turns 90 years old this weekend! It has been a crazy life for Shotgun Willie, but he doesn’t show signs of slowing down— even as he approaches the century mark.