For information on specific players,
Please check out the Bios page

Radio, Newspapers, and Print Media were the primary ways in which people consumed information and entertainment before television or the internet. To understand The Skyline Boys’ origin story, it’s useful to have a sense of how instrumental these media were for musicians and audiences of their era. 

In the past, radio stations broadcast live music, comedy, acts, and skits. The Skyline Boys featured on many Mid-Atlantic region stations, like WSVA, WCHA, WFMD, WJEJ, and WYVE. The radio phenomenon for folk music, considered early country, originated with “The Grand Ole Opry,” also known by the tag WSM. “The World’s Original Jamboree,” aka WWVA, is the second-oldest U.S. station. And yet another was WRVA, known for the “Old Dominion Barn Dance,” which followed the format. This is only scratching the surface of the depth of radio.

The Skyline Boys were specifically cast members of WWVA and WRVA. They got started and networked in what we would consider a regional scene. WWVA and WRVA featured many artists from American folklore, and local newspapers shared broadcast schedules of different performances happening regionally. Newspapers have been key in uncovering details about the real origins of The Skyline Boys of the 1940s-1950s. For the first time, please enjoy a timeline of their formation.

The Skyline Boys. 
Formed in 1941, per the Orange and Purple songfolio (released later in their career with a different lineup). Visit the Ephemera page to review songfolios and pamphlets.

There was a group called the “Virginia Skyline Boys” that appeared on the WPUV radio schedule in the Southwest Times and through WYVE in the early to mid-1940s. A photo of that group (unavailable) was reviewed in 2023 via the Wytheville, Virginia Department of Museums. The “Virginia Skyline Boys” was a different group of players. It’s possible that ‘The Skyline Boys’ featured on this website adopted the name, or perhaps knew the “Virginia Skyline Boys.” This is purely a geographic proximity-based hypothesis and is unlikely to be verified.

‘The Skyline Boys’ name, per this website, did not show up in newspapers until approx. 1947. Based on the 1941 timeframe, the members would have been in their late teens and early twenties when they started using the name. It is worth noting that many members served in the Armed Forces across different branches and timelines, leading up to or during WWII. Several other music groups featuring the founding members were identified ahead of the formation of ‘The Skyline Boys.’

In 1943, Dude Webb, Bill Bailey, and Buck Ryan are photographed as a WSVA group. 1944 and 1945, members “Sweet” Bill Bailey, “Lone Texan” Dude Webb, “Cowboy” Slim Hank Silby, and “Fiddlin” Buck Ryan were identified as players with “Uncle Joe and his Barndance Gang.” In 1946, “Dude Webb’s Valley Playboys” featured Bill Bailey and Hank Silby. 

WSVA Harrisonburg, VA 1943
L-R: Unk., Dude Webb
Buck Ryan, Bill Bailey, Unk.
Source: Londa Parks, Dicky Parks
Photocopy of an original photograph

“Uncle Joe & His Barndance Gang”
Source: The Daily Progress
Charlottesville, VA. April 12, 1944, Pg. 2

“Uncle Joe & His Barndance Gang”
Source: The Evening Leader
Staunton, VA. Sept. 22, 1945, Pg. 6

Dude Webb’s Valley Playboys
Source: The Daily Newsleader
Staunton, VA. June 27, 1946, Pg. 7

Toby Stroud’s “Blue Mountain Boys” of 1946 were the core lineup of members who formed The Skyline Boys, on which this website is based. The earliest associated names are Bill Bailey, Roy Parks, Hank Silby (aka Quincy Snodgrass), and Dude Webb. “Bud Messner and The Skyline Boys” and other variations, such as “The Skyliners” and combinations of “His/The,” evolved. Their naming variants were influenced by the roster of the time and how they chose to be presented. Bud Messner was linked with The Skyline Boys, from a naming perspective, around Aug/Sept 1947. Bud Messner and The/His Saddle Pals, and The Skyline Boys, were all broadcasting from WCHA in 1947. They played shows together before Bud became the frontman. Dude Webb was initially the frontman for The Skyline Boys in early 1947. By the end of 1947, Bud Messner took root in the name.

Ernest Tubb, Shade Gap
The Skyline Boys & Saddle Pals
A Bud Messner Promotion
Source: Public Opinion
Chambersburg, PA. May 26, 1947, Pg. 4

Jimmie Wakely, Conomac Park
Dude Webb & His Skyline Boys
Source: The Herald-Mail
Hagerstown, MD. July 25, 1947, Pg. 5

Firemen’s Carnival
Bud Messner & His Saddle Pals
Dude Webb & His Skyline Boys
Source: The Gettysburg Times
Gettysburg, PA. Aug. 8, 1947, Pg. 6

Hi-Way Theater, Ickesburg, PA
Bud Messner & Dude Webb
The Skyline Boys (Formation)
Source: The Perry County Times
New Bloomfield, PA. Sept. 18, 1947, Pg. 9

Bud & The Skyline Boys, 1947
L-R: Bud Messner, Bill Bailey
Dude Webb, Roy Parks
Source: Green Songfolio
Private Collection

An estimated first photo of The Skyline Boys is shown below. There is no date. The names Roy, Hank, and Bill are on the back. The print is on thick paper and is somewhat strange; possibly a copy of a copy, or similar. With details around the name being unclear before 1946, it’s uncertain when this picture was originally taken. The best guess based on their appearance is 1946 or earlier. Dude Webb is not shown; it is possible that this photo was intended to depict Toby Stroud’s “Blue Mountain Boys.”

The Skyline Boys
Est. 1st Photo, 1946 – early 1947
L-R: Roy Parks, Hank Silby (Quincy), Bill Bailey
Source: Private Collection

A picture album featuring photos of Dude Webb, Bill Bailey, and Roy Parks is estimated to be the first promotional release using the name. There is a group photo including Hank Silby in character as the early Quincy Snodgrass. Hank Silby does not have an individual photo in the picture album. There is no specific date printed anywhere on the cover, back, or inside. In 2025, a second copy of the album was located. That second copy has a written mailing address of WCHA Chambersburg, which aligns with a timeframe of approximately 1947. 

The network of musicians associated with WWVA, among others, was a mutual connection for The Skyline Boys. Bill Bailey appears to be the first member of The Skyline Boys associated with WWVA. Bill was photographed with Toby Stroud and Buck Ryan in 1944. In 1946, Bill Bailey, Roy Parks, and Dude Webb are pictured as WWVA cast alongside Toby Stroud, Pete Cassel, and Hawkshaw Hawkins, among other iconic names of the era. The same year, Bill Bailey, Roy Parks, and Hank Silby are photographed with Toby Stroud as “The Blue Mountain Boys.” Whether Toby Stroud or Buck Ryan recordings of the mid-1940s feature members of The Skyline Boys remains unconfirmed, but is highly plausible. Interestingly, the photo of Toby Stroud, Buck Ryan, and Bill Bailey is in the credits booklet for the “Early Days of Bluegrass” Vol. 2 LP. The booklet states recordings were done with Buck, Bill, and an unknown bassist.

WWVA 1946
Jamboree Cast
Source: WV Department of Culture and History

WWVA 1946 Cast (As Shown): (Back Row) L-R: Shorty Fincher, Bob Thomas, Smilie Sutter, Sandy Edwards, Joe Barker, Hawkshaw Hawkins, Jimmie Hutchinson, Dick Lanning, Curly Collins, Bud Kissenger, Jack Gillette (Middle Row) L-R: Rawhide, Boy Huey, Clyde Fogel, Little Sampson, Red Belcher, Reed Dunn, Pete Cassell, Sonny Davis, Roy Parks, Bill Bailey, Benny Kissnger, Dude Webb (Front Row) L-R: Wyn Sheldon, Sally FIncher, Millie Wayne, Bonnie Baldwin, Shirley Barker, Honey Davis, Eileen Newcomer, Maxine Newcomer, Lew Clawson

Roy Parks is believed to have recorded with Pete Cassel, determined by a highlight “mixtape” cassette. The other Skyline Boys may have played with Pete, too. Roy’s cassette includes both Pete Cassel and The Skyline Boys tunes, nineteen songs filling both sides. Roy left the cassette to his brother James H. Parks in the 1980s-1990s. James passed on the cassette for preservation in 2024. Roy likely captured the songs from a combination of shellac, reel, and 33/45 to a tabletop cassette recorder. There is audible room noise on the cassette. Roy did not share any details with James about the contents or recordings. The connection to Pete Cassel was discovered during the digitization process. No details about Pete Cassel were known to the Parks family prior to this finding.

This clue about The Skyline Boys’ proximity to Pete Cassel would not have been known without the contribution of James H. Parks. Their WWVA 1946 mutual cast status is a likely conclusion. Pete Cassel has been described as “the man who gave the most to country music and received the least in return.” He had the moniker “The Blind Minstrel,” as he was blinded by eye medication as a child. Pete may have been a figure to the Boys. As their elder, a notion of influence during the early years of Roy and the Boys’ career is viable.

On the back of the Pete Cassel photo below is a handwritten note penned by Toby Stroud on behalf of Pete: signed Cassel, one L. 

WWVA 1940s
Pete Cassel, The Blind Minstrel (1917-1954)
Source: Private Collection

Roy Parks “Mixtape” Cassette
Original Audio, est. 1946-1950s
78 Records > Cassette (1970s) > Digital (2024)
Source: Private Collection

Jimmy Dean’s Town & Country Show (1954)
feat. Quincy Snodgrass (13:18) & Pete Cassel (18:14)
Source: YouTube Upload by User: GatorRock 

Quincy Snodgrass, Roy Parks, and Slim Roberts of The Skyline Boys were WRVA’s “Old Dominion Barn Dance” cast members for about four months in 1950. An article from Spring 1950 noted that they left the WRVA Barn Dance to go on tour with Tex Ritter. Renee Collins Cobb and her father, Phil Collins, were kind enough to share a couple of photos of original fliers featuring members of The Skyline Boys. Cast member Curley was Renee’s grandfather. One of the photos they shared was for a farewell show for Quincy, Roy, and Slim ahead of the Tex Ritter U.S. and Canadian tour of 1950… Thanks for this cool contribution.

WRVA March 1950
Old Dominion Barn Dance
Feat. members The Skyline Boys
Source: Photo. Renee Collins Cobb, Phil Collins
Original Source: Richmond Times Dispatch (March 4, 1950)

WRVA May 1950
Old Dominion Barn Dance
Feat. The Skyline Boys members
Source: Photo. Renee Collins Cobb, Phil Collins
Original Source: Richmond Times Dispatch (May 20, 1950)