In terms of breaking it, it depends on the type of rim - there are those with suspension like in the NBA and there are cheaper ones such as driveway hoops that probably aren't in most cases. These are the ones that are most likely to break.
In terms of rules - if you hang on the rim for an excessive amount of time you can receive a technical foul.
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Yes it is illegal , For safety reasons beacuse if you got so much momentum you, will probaly fall down and break your head