Classic American singer-songwriter Roger Miller knew how to have a good time. The self-styled "King of the Road" was known for his love of novelty songs and his ability to turn a quick phrase.

Miller's music career began in the late 1950s. He was purely a songwriter at first, but he blossomed as a performer in the 1960s, during the era of the Nashville Sound. The Boot's list of Miller's Top 5 songs encompasses both his silly side and his more contemplative moments.

  • 5

    "Oo-de-Lally"

    From the 'Robin Hood' Soundtrack (1973)

    Miller was a man of many talents, and he put several of them -- songwriting, singing and acting -- together for the 1973 animated Disney film Robin Hood. Miller voiced Alan-a-Dale, the rooster who narrates the story, and wrote and performed three songs for the movie, including the delightful walking song that drove the film, “Oo-de-Lally.” If it’s been a while since you’ve seen Robin Hood, all it takes is a listen to Miller singing, “Robin Hood and Little John, walking through the forest / Laughin’ back and forth and what the other has to say / Reminiscin’, this-and-thattin’, havin’ such a good time / Oo-de-lally, oo-de-lally, golly, what a day” to feel like you’re right back in Sherwood Forest.

  • 4

    "Chug-a-Lug"

    From 'Roger and Out' (1964)

    He wrote a lot of good, wholesome songs, but make no mistake: Miller also had a reputation as a party boy who liked to drink and have a lot of (sometimes too much) fun. “Chug-a-Lug” is the perfect representation of that part of Miller, a silly, catchy, song the only goal of which is to celebrate Miller’s storied history of getting plastered. And who could forget its classic drinking chorus: “Chug-a-lug, chug-a-lug / Make you want to holler 'Hi-de-do!' / Burns your tummy, don’tcha know / Chug-a-lug, chug-a-lug.

  • 3

    "Old Friends"

    From 'Old Friends' (1982)

    “Old Friends” is a good song all on its own, but it also has an important place in country music history. Written by Miller, it's the title track of his collaborative 1982 album with Willie Nelson, and features additional vocals from Ray Price.

    "Old Friends" was Miller’s last Top 20 hit, his highest charting song since 1973’s “Open Up Your Heart.” It became important again decades later, too: Nelson recorded a new version for 2019’s Old Friends (Live) album, this time featuring Kris Kristofferson and Merle Haggard. It would turn out to be one of the last songs Haggard had recorded before his death.

  • 2

    "Dang Me"

    From 'Roger and Out' (1964)

    “Dang Me” defied the odds: Despite being a novelty song with lyrics including “Roses are red and violets are purple / Sugar is sweet and so is maple surple,” and despite clocking in at under two minutes, it became a big hit for Miller. In fact, it was his first country song to top the charts, spending 25 weeks in the No. 1 spot, and also became a Top 10 pop crossover hit. “Dang Me,” released in 1964, also won Miller the Grammy for Best Country & Western Song.

  • 1

    "King of the Road"

    From 'The Return of Roger Miller' (1965)

    Miller’s celebration of a vagabond living a free life on the road turned into the biggest hit of his career. “King of the Road” was Miller’s fifth single, and it instantly became a crossover hit, landing at No. 1 on the Billboard country charts, No. 4 on the Billboard Hot 100 and No. 1 on the Easy Listening chart. “King of the Road” was nominated for three Grammys: Song of the Year, Record of the Year and Best Vocal Performance, Male, and when Miller was posthumously inducted into the Country Music Hall of Fame, it's the song that Merle Haggard, Willie Nelson, Dolly Parton, Marty Stuart and Dwight Yoakam chose to perform to honor him.