1877 US in baseball; metaphorical usage from 1896, more generally from 1930. Since at least 1870, baseball teams would reissue tickets in case of postponement due to rain, which became known as rain checks.
Update: In fact, the latest update of iPhoto is using Helvetica Neue. And now there's Avenir, a Linotype typeface and Apple's new favorite. It was designed by Adrian Frutiger in 1988, inspired by two old school typefaces created in the 20s: Erbar by Jakob Erbar and Futura by Paul Renner.
Here Caxton introduces his book to the reader. The typeface is inspired by the Gothic or black letter script, common across northern Europe. The sets of type were designed for languages such as Middle Dutch which did not use the traditional English letters yogh, eth (Ã°) and thorn (Ã¾).