Sus primeras grabaciones conocidas fueron para la Michigan Electric Company de Detroit, que fabricaba cilindros baratos, de un centavo, para las salas recreativas. Una demo que hizo en octubre de 1898 llamó poderosamente la atención de Edison Records, que lo fichó como miembro del Haydn Quartet, reemplazando al también tenor Jere Mahoney.
En febrero de 1900 deja la Berliner y firma un contrato con la Victor Talking Machine, donde compagina su trabajo como cantante con el de director ejecutivo de la sede de Nueva York, supervisando no solo el repertorio, sino también los contratos que la compañía firmaba con los artistas y las editoras de música.
Macdonald ascendió rápidamente en Victor, convirtiéndose en su gerente de ventas nacional en 1920 y gerente de artistas y repertorio en 1923, pero en 1925 fichó como técnico para Columbia, compañía en la que permaneció hasta su muerte.
De entre sus más de 60 éxitos destacan "Absence Makes the Heart Grow Fonder", "The Tale of the Bumble Bee" (1901), "The Mansion of Aching Hearts" (1902), "Hiawatha" (1903), "My Dear" (1907), "Where the River Shannon Flows", "In the Valley of Yesterday" (1910), "Down by the Old Mill Stream" (1911) y "The Girl on the Magazine" (1916), todos ellos números uno.
1900. Berliner 0801. Mandy Lee (#3, 10.03.1900) 🔊
1900. Berliner 0940. My Sunny Southern Home (#2, 16.06.1900)
1900. Berliner 0940. My Sunny Southern Home (#2, 16.06.1900)
1900. Edison 7587. A Bird In A Gilded Cage (#2, 20.10.1900)
1900. Edison 7595. I Can´t Tell Why I Love You, But I Do (#2, 10.11.1900)
1900. Edison 7595. I Can´t Tell Why I Love You, But I Do (#2, 10.11.1900)
1900. Edison 7610. I Love You Just The Same (#4, 01.12.1900)
1901. Edison 7789. Hearts And Flowers (#4, 08.06.1901)
1901. Edison 7942. I´ll Be With You When The Roses Bloom Again
1901. Edison 7942. I´ll Be With You When The Roses Bloom Again
(#3, 21.12.1901)
1903. Edison 8353. Two Eyes Of Blue (#5, 02.05.1903)
1903. Edison 8425. Hiawatha (#1, 04.07.1903)
1903. Edison 8526. By The Sycamore Tree (#3, 26.12.1903)
1903. Edison 8425. Hiawatha (#1, 04.07.1903)
1903. Edison 8526. By The Sycamore Tree (#3, 26.12.1903)
1905. Edison 9054. Dearie (#6, 30.09.1905)
1906. Edison 9344. Where The River Shannon Flows (#2, 22.09.1906)
1901. Gram-o-Phone 55. In The Shade Of The Palm (#3, 21.09.1901)
1900. Gram-o-Phone 94. The Holy City (#2, 24.11.1900)
1901. Gram-o-Phone 55. In The Shade Of The Palm (#3, 21.09.1901)
1900. Gram-o-Phone 94. The Holy City (#2, 24.11.1900)
1900. Gram-o-Phone 99. My Wild Irish Rose (#3, 06.10.1900)
1900. Gram-o-Phone 533. I Can´t Tell Why I Love You, But I Do
1901. Gram-o-Phone 652. When The Harvest Days Are Over (#2, 11.05.1901)
1901. Gram-o-Phone 655. Good-Bye, Dolly Gray (#2, 18.05.1901)
1901. Gram-o-Phone 655. Good-Bye, Dolly Gray (#2, 18.05.1901)
1901. Victor 769. When You Were Sweet Sixteen (#3, 17.08.1901) 🔊
1900. Edison 7558. When We Are Married (#2, 08.09.1900)
1901. Edison 7758. Tell Me, Pretty Maiden (#1, 27.04.1901)
Harry Macdonough & John Bieling
1899. Berliner 0552. Just As The Sun Went Down (#4, 02.12.1899)
1901. Victor 907. Absence Makes The Heart Grow Fonder (#1, 12.10.1901)
1901. Victor 908. The Tale Of The Bumble Bee (#1, 05.10.1901)
1901. Victor 909. I´ve A Longing In My Heart For You, Louise (#3, 12.10.1901)
1901. Victor 908. The Tale Of The Bumble Bee (#1, 05.10.1901)
1901. Victor 909. I´ve A Longing In My Heart For You, Louise (#3, 12.10.1901)
1901. Victor 951. The Wedding Of Reuben And The Maid (#4, 21.12.1901)
1902. Victor 1214. Home, Sweet Home (#3, 26.04.1902)
1902. Victor 1214. Home, Sweet Home (#3, 26.04.1902)
1902. Victor 1269. My Carolina Lady (#4, 07.06.1902)
1902. Victor 1329. Bye And Bye You Will Forget Me (#4, 15.02.1902)
1902. Victor 1391. On A Sunday Afternoon (#5, 16.08.1902)
1902. Victor 1393. Josephine, My Jo (#4, 30.08.1902)
1902. Victor 1395. Jennie Lee (#3, 30.08.1902)
1902. Victor 1415. The Mansion Of Aching Hearts (#1, 13.09.1902)
1902. Victor 1617. My Beautiful Irish Maid (#3, 06.12.1902)
1903. Victor 1655. In The Good Old Summer Time (#2, 24.01.1903)
1902. Victor 1395. Jennie Lee (#3, 30.08.1902)
1902. Victor 1415. The Mansion Of Aching Hearts (#1, 13.09.1902)
1902. Victor 1617. My Beautiful Irish Maid (#3, 06.12.1902)
1903. Victor 1655. In The Good Old Summer Time (#2, 24.01.1903)
1903. Victor 1920. Heidelberg (#3, 16.05.1903)
1903. Victor 1922. Since I First Met You (#4, 23.05.1903)
1903. Victor 2332. Beautiful Bird, Sing On (#2, 05.09.1903) con Joe Belmont
1903. Victor 2458. When Kate And I Were Comin´ Thro The Rye
(#4, 12.12.1903)
1904. Victor 2515. I Love Only One Girl In The Wide, Wide World
1904. Victor 2515. I Love Only One Girl In The Wide, Wide World
(#3, 16.01.1904)
1904. Victor 2565. The Girl You Love (#5, 13.02.1904)
1904. Victor 2574. Peggy Brady (#5, 27.02.1904)
1904. Victor 2656. Navajo (#3, 30.04.1904)
1904. Victor 2656. Navajo (#3, 30.04.1904)
1904. Victor 2697. My San Domingo Maid (#5, 25.06.1904)
1904. Victor 2851. Good-Bye, My Lady Love (#5, 03.09.1904)
1905. Victor 4062. My Cozy Corner Girl (#7, 28.01.1905)
1905. Victor 4132. Sweet Thoughts Of Home (#3, 28.01.1905)
1905. Victor 4132. Sweet Thoughts Of Home (#3, 28.01.1905)
1905. Victor 4272. You And I (#9, 29.04.1905) con Florence Hayward
1905. Victor 4504. In The Valley Of Yesterday (#3, 09.12.1905)
1905. Victor 4504. In The Valley Of Yesterday (#3, 09.12.1905)
1906. Victor 4601. If A Girl Like You Loved A Boy Like Me (#4, 28.04.1906)
1906. Victor 4665. When The Mocking Birds Are Singing (#6, 28.04.1906)
1906. Victor 4672. My Old Kentucky Home (#3, 23.06.1906)
1906. Victor 4828. Ain´t You Coming Back To Old New Hampshire?
1906. Victor 4672. My Old Kentucky Home (#3, 23.06.1906)
1906. Victor 4828. Ain´t You Coming Back To Old New Hampshire?
(#3, 10.11.06)
1907. Victor 4871. In The Evening By The Moonlight, Dear Louise
1907. Victor 4871. In The Evening By The Moonlight, Dear Louise
(#3, 05.01.07)
1907. Victor 5121. The Tale The Church Bell Tolled (#3, 15.07.07)
1907. Victor 5176. Sweet Julienne (#5, 07.09.07)
1907. Victor 5189. Dreaming (#6, 26.10.07)
1907. Victor 5293. My Dear (#1, 14.12.07)
1907. Victor 5293. My Dear (#1, 14.12.07)
1907. Victor 31672. Messiah: Every Valley Shall Be Exalted (#9, 28.12.07)
1910. Victor 16440. Where The River Shannon Flows (#1)
1910. Victor 16535. In The Valley Of Yesterday (#1)
1911. Victor 17000. Down By The Old Mill Stream (#1)
1912. Victor 17057. When Irish Eyes Art Smiling (#3)
1913. Victor 17401. There´s A Girl In The Heart Of Maryland (#2)
1916. Victor 17889. Araby (#3)
1916. Victor 17945. The Girl On The Magazine (#1)
1910. Victor 16535. In The Valley Of Yesterday (#1)
1911. Victor 17000. Down By The Old Mill Stream (#1)
1912. Victor 17057. When Irish Eyes Art Smiling (#3)
1913. Victor 17401. There´s A Girl In The Heart Of Maryland (#2)
1916. Victor 17889. Araby (#3)
1916. Victor 17945. The Girl On The Magazine (#1)
1905. Columbia 32687. Tale Of The Turtle Dove (#6, 24.06.1905)
Harry Macdonough & S.H. Dudley
1899. Edison 7262. ´Mid The Green Fields Of Virginia (#2, 18.11.1899)
1901. Victor 775. Sweet Annie Moore (#3, 24.08.1901)
1903. Victor 2056. Tessie (#4, 11.07.1903)
Harry Macdonough & Grace Spencer
1900. Edison 7558. When We Are Married (#2, 08.09.1900)
1901. Edison 7758. Tell Me, Pretty Maiden (#1, 27.04.1901)
1902. Victor 1362. Tell Me, Pretty Maiden (1902) 🔊
1899. Berliner 0552. Just As The Sun Went Down (#4, 02.12.1899)
1903. Victor 1855. In the Sweet Bye and Bye (#1, 25.04.1903)
1907. Victor 4877. A Flower From Home, Sweet Home (#8, 26.01.1907)
1908. Victor 5506. Over the Hills and Far Away (#2)
1905. Edison 8938. Marguerite (#3, 18.03.1905)
1905. Edison 8938. Marguerite (#3, 18.03.1905)
Harry Macdonough & Elise Stevenson
1907. Victor 5020. Because You're You (#1, 20.04.07)
1908. Victor 5340. I Love You So (#3, 22.02.08)
1908. Victor 5446. Kiss Duet (#3)
1909. Victor 16259. Shine On, Harvest Moon (#1)
Harry Macdonough & Lucy Isabelle Marsh
1910. Victor 5784. Every Little Movement (#1)
1917. Victor 18172. Babes in the Wood (#2)
1915. Victor 17858. Auf Wiedersehen (#2)
1915. Victor 35491. They Didn't Believe Me (#1)
1907. Victor 5020. Because You're You (#1, 20.04.07)
1908. Victor 5340. I Love You So (#3, 22.02.08)
1908. Victor 5446. Kiss Duet (#3)
1909. Victor 16259. Shine On, Harvest Moon (#1)
Harry Macdonough & Frank Stanley
1907. Victor 4917. Almost Persuaded (#8, 23.02.07)
1908. Victor 5368. Some Day You´ll Come Back To Me (#4, 28.03.08)
Harry Macdonough & Lucy Isabelle Marsh
1910. Victor 5784. Every Little Movement (#1)
1917. Victor 18172. Babes in the Wood (#2)
Harry Macdonough & Olive Kline
1915. Victor 17858. Auf Wiedersehen (#2)
1915. Victor 35491. They Didn't Believe Me (#1)