Singing style and vocal characteristics
Crosby was one of the first singers to exploit the intimacy of the microphone, rather than using the deep, loud "vaudeville style" associated with All Jolson and others. Crosby's love and appreciation of jazz music helped bring the genre to a wider mainstream audience. Within the framework of the novelty singing style of The Rhythm Boys, Crosby bent notes and added off-tune phrasing, an approach that was firmly rooted in jazz. He had already been introduced to Louis Armstrong and Bessie Smith prior to his first appearance on record. Crosby and Armstrong would remain professionally friendly for decades, notably in the 1956 film High Society, where they sang the duet "Now You Has Jazz."
Thoroughbred horse racing
Crosby was a fan of thoroughbred horse racing and bought his first racehorse in 1935. In 1937, he became a founding partner of the Del Mar Thoroughbred Club and a member of its Board of Directors. Operating from the Del Mar Racetrack at Del Mar, California, the group included millionaire businessman Charles S. Howard, who owned a successful racing stable that included Seabiscuit. His son, Lindsay Howard, became one of Crosby's closest friends; Crosby named his son Lindsay after him, and would purchase his 40-room Hillsborough estate from Lindsay in 1965.
Crosby the sportsman
We had to keep a close watch on our actions... When one of us left a sneaker or pair of underpants lying around, he had to tie the offending object on a string and wear it around his neck until he went off to bed that night. Dad called it "the Crosby lavalier." At the time the humor of the name escaped me... "Satchel Ass" or "Bucket Butt" or "My Fat-assed Kid." That's how he introduced me to his cronies when he dragged me along to the studio or racetrack... By the time I was ten or eleven he had stepped up his campaign by adding lickings to the regimen. Each Tuesday afternoon he weighed me in, and if the scale read more than it should have, he ordered me into his office and had me drop my trousers... I dropped my pants, pulled down my undershorts and bent over. Then he went at it with the belt dotted with metal studs he kept reserved for the occasion. Quite dispassionately, without the least display of emotion or loss of self-control, he whacked away until he drew the first drop of blood, and then he stopped. It normally took between twelve and fifteen strokes. As they came down I counted them off one by one and hoped I would bleed early... When I saw Going My Way I was as moved as they were by the character he played. Father O'Malley handled that gang of young hooligans in his parish with such kindness and wisdom that I thought he was wonderful too. Instead of coming down hard on the kids and withdrawing his affection, he forgave them their misdeeds, took them to the ball game and picture show, taught them how to sing. By the last reel, the sheer persistence of his goodness had transformed even the worst of them into solid citizens. Then the lights came on and the movie was over. All the way back to the house I thought about the difference between the person up there on the screen and the one I knew at home.
Failing health and death
- "That's Grandma" (1927), with Harry Barris and James Cavanaugh
- "From Monday On" (1928), with Harry Barris and recorded with the Paul Whiteman Orchestra featuring Bix Beiderbecke on cornet, no. 14 on US pop singles charts
- "What Price Lyrics?" (1928), with Harry Barris and Matty Malneck
- "At Your Command" (1931), with Harry Barris and Harry Tobias, US, no. 1 (3 weeks)
- "Where the Blue of the Night (Meets the Gold of the Day)" (1931), with Roy Turk and Fred Ahlert, US, no. 4; US, 1940 re-recording, no. 27
- "I Don’t Stand a Ghost of a Chance With You" (1932), with Victor Young and Ned Washington, US, no. 5
- "My Woman" (1932), with Irving Wallman and Max Wartell
- "Love Me Tonight" (1932), with Victor Young and Ned Washington, US, no. 4
- "Waltzing in a Dream" (1932), with Victor Young and Ned Washington, US, no.6
- "I Would If I Could But I Can't" (1933), with Mitchell Parish and Alan Grey
- "Where the Turf Meets the Surf" (1941)
- "Tenderfoot" (1953)
- "Domenica" (1961)
- "That's What Life is All About" (1975), with Ken Barnes, Peter Dacre, and Les Reed, US, AC chart, no. 35; UK, no. 41
- "Sail Away to Norway" (1977)
- The Radio Singers (1931, CBS), sponsored by Warner Brothers, 6 nights a week, 15 minutes.
- The Cremo Singer (1931–1932, CBS), 6 nights a week, 15 minutes.
- Unsponsored (1932, CBS), initially 3 nights a week, then twice a week, 15 minutes.
- Chesterfield's Music that Satisfies (1933, CBS), broadcast two nights, 15 minutes.
- Bing Crosby Entertains for Woodbury Soap (1933–1935, CBS), weekly, 30 minutes.
- Kraft Music Hall (1935–1946, NBC), Thursday nights, 60 minutes until January 1943, then 30 minutes.
- Armed Forces Radio (1941–1945; World War II).
- Philco Radio Time (1946–1949, ABC), 30 minutes weekly.
- The Bing Crosby ChesterfieldShow (1949–1952, CBS), 30 minutes weekly.
- The Minute Maid Show (1949–1950, CBS), 15 minutes each weekday morning; Bing as disc jockey.
- The General Electric Show (1952–1954, CBS), 30 minutes weekly.
- The Bing Crosby Show (1954–1956, CBS), 15 minutes, 5 nights a week.
- A Christmas Sing with Bing (1955–1962, CBS, VOA and AFRS), 1 hour each year, sponsored by the Insurance Company of North America.
- The Ford Road Show (1957–1958, CBS), 5 minutes, 5 days a week.
- The Bing Crosby – Rosemary Clooney Show (1958–1962, CBS), 20 minutes, 5 mornings a week, with Rosemary Clooney.
- Flying down to Rio* (1933)
- The Gay Divorcee* (1934)
- Top Hat* (1935)
- The Good Fairy (1935)
- Diamond Jim (1935)
- I Dream Too Much (1935)
- The Ex-Mrs. Bradford (1936)
- Piccadilly Jim (1936)
- Swing Time* (1936)
- It’s Love I’m After (1937)
- Quality Street (1937)
- Shall We Dance* (1937)
- Breakfast for Two (1937)
- Swiss Miss (1938)
- Island of Lost Men (1939)
- The Lone Wolf Strikes (1940)
- 'Til We Meet Again (1940)
- The Lone Wolf Meets a Lady (1940)
- The Boys from Syracuse (1940)
- The Lone Wolf Keeps a Date (1940)
- The Lady Eve (1941)
- The Lone Wolf Takes a Chance (1941)
- Road to Zanzibar (1941)
- Secrets of the Lone Wolf (1941)
- Sullivan’t Travels (1941)
- The Shanghai Gesture (1941)
- Counter-Espionage (1942)
- The Moon and the Sixpence (1942)
- Forever and a Day (1943)
- Heavenly Music (1943 short)
- The Sky’s the Limit (1943) (uncredited)
- Submarine Base (1943)
- Passport to Suez (1943, part of the Lone Wolf series)
- Holy Matrimony (1943)
- The Notorious Lone Wolf (1946)
- The Lone Wolf in Mexico (1947)
- The Lone Wolf in London (1947)
- Romance on the High Seas (1948)
- The Adventures of Ichabod and Mr. Toad (1949 short) - voice of J. Thaddeus Toad
- Love Happy (1949)
- Fancy Pants (1950)
- Bowery to Bagdad (1955)