He began as a bit-part funny-man hailing from Toledo, OH. He started out doing a vaudeville routine with Lolly Gookins called Cliff and Lolly Nuts of Harmony. He developed a character called Charley Weaver, who was a hapless folksy old man. It caught on. (He later got into a cross-dressing bit that was big for a time.) An issue of Popular Science from 1938 called him a "Radio Comedian" noting that he was playing more than 50 parts in various NBC radio programs. That's a nice early and reliable print source, but it cites no programs or stations!
Below is a partial list of programs he appeared on. I got some from the Radio Gold Index, more from the Encyclopedia of Old Time Radio by John Dunning. I cant' confirm it, but many of those NBC programs were performed at WBCN, the Chicago NBC affiliate. To be honest I can't find 13 programs happening concurrently in the Chicago metro but there are more enough a few to bear this out. His uncredited appearances are surely far greater.
- WGN - Cliff and Lolly, 1933
- WISN - Myrt and Marge, 1933 -?
- NBC - The Fred Astaire (Packard) Show, 1934-1937
- KECA - Hollywood Spotlight, 1935
- NBC - Edgar A. Guest, 1935-1941
- WMAQ - Fibber McGee and Molly, 1936-1954
- NBC Blue - The Jack Benny (Jell-O) Program, 1938
- NBC Blue - The Rudy Vallee (Fleischmann's Yeast ) Hour, 1939
- NBC Blue - Avalon Time, 1939-1941
- NBC Blue - Frank Watanabe and The Honorable Archie, 1939-1940
- ABC - Point Sublime, 1940-1948
- NBC Blue - I Love a Mystery, 1942?
- Mutual - The Adventures of Wild Bill Hickok, 1943-1953
- NBC - The Lifebuoy Show, 1943
- ABC - Glamour Manor, 1944-1945
- NBC - The Dick Haymes (Autolite) Show, 1944-1948
- ABC - Ellery Queen, 1948
- CBS - My Home Town, 1949
- The Dave Willock and Cliff Arquette Show, 1950
- CBS - Lum and Abner Show, 1950
- CBS - The Harold Peary Show, 1951
There is a stretch in his career when he was clearly based in the Chicago area. It starts in 1933 or earlier and running until about 1938 when his career clearly became more mobile. The Chicago river hugs Wacker Drive right through the heart of the city, splitting into the north and south branches at Orleans Street. In that era WGN was in the Drake Hotel on Lakeshore Drive. 14 blocks north of the river—but only two if you boated out and around to the Lake Michigan side. WISN however, is up in Milwaukee. It's a trip not directly traversed by any river route, nor in a time frame allowing one to appear on multiple shows per day.
But WMAQ moved to 400 West Madison in 1928 (today 2 North Riverside Plaza) and that location is 1 block off Wacker drive following the south branch. As of 1935 downtown Chicago had at least 8 commercial radio stations: WCRW, WMAQ, WENR, WGN, WBCN, WBBM, WGES, WHFC, WKBI, and WSBC. WGES was on 2400 W. Madison Street in that era, and the NBC Tower at 454 N. Columbus Drive. I have to say... this at least appears plausible.