You can connect a Converter Box to a VCR, but there are some problems. Most of the digital to analog converter boxes have limited capability. VCRs will not work the same as they do now when connected to a converter box.
Unfortunately, you will not be able to record one progam while watching another.
Most converter boxes are not programmable like a VCR and cannot switch to a specified channel at a set time.
Update: The DISH Network DTVPal, DISH Network TR-40CRA, DISH Network DTVPal Plus, Zinwell ZAT-950A and the Zinwell ZAT-970A have a (VCR) Event Timer. You can program these boxes to turn on and record a specific channel at a specific time BUT you still can not record one channel and watch other.
The Zinwell ZAT-970A is the only box being sold now as far as we know.
VCRs will only record whatever channel the converter box is already set on. If you want to keep your old VCR and use it with a converter box, you need to program your VCR to record channel 3 or 4, and tune your converter box to the channel you want to record.
Another problem is that the converter box has an energy saving feature that will cause the box to shut off automatically if not in use, but that feature can be disabled.
Unfortunately, there just isn’t an easy solution to this very annoying problem.
You may want to buy a digital recorder such as a DVD recorder or DVR (TiVo) with a digital (ATSC) tuner that will also replace the need for a converter box.